Herbicidal O-alkylsulfonyloxy- and O-alkylsulfonylaminobenzenesulfonamides

ABSTRACT

N-(heterocycliccarbamoyl)arylsulfonamides, such as N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-hydroxybenzenesulfonamide, methanesulfonate are useful for plant growth retardation, brush control and weed control in crops.

RELATED APPLICATION

This is a division of application Ser. No. 544,429, filed Oct. 21, 1983, now U.S. Pat. No. 4,534,789, which is a continuation-in-part of my copending application U.S. Ser. No. 262,813, filed May 19, 1981, now abandoned which in turn is a continuation-in-part of my copending application U.S. Ser. No. 168,344, filed July 11, 1980, now abandoned.

BACKGROUND OF THE INVENTION

This invention relates to ortho(sulfonyl)oxybenzene sulfonamides and their use as herbicides.

Netherlands Pat. No. 121,788, published Sept. 15, 1966, teaches the preparation of compounds of Formula (I), and their use as general or selective herbicides: ##STR1## wherein R₁ and R₂ may independently be alkyl of 1-4 carbon atoms; and

R₃ and R₄ may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms.

Compounds of Formula (II), and their use as antidiabetic agents, are reported in J. Drug. Res. 6, 123 (1974): ##STR2## wherein R is pyridyl.

In U.S. Pat. No. 4,127,405, compounds are disclosed of the general formula: ##STR3## wherein R₁ is ##STR4## R₃ and R₆ are independently hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, trifluoromethyl, cyano, CH₃ S(O)_(n) --or CH₃ CH₂ S(O)_(n) --;

R₄ is hydrogen, fluorine, chlorine, bromine or methyl;

R₅ is hydrogen, fluorine, chlorine, bromine, methyl or methoxy;

R₇ is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms or alkoxy of 1-2 carbon atom;

R₈ is hydrogen, methyl, chlorine or bromine;

R₉ and R₁₀ are independently hydrogen, methyl, chlorine or bromine;

W and Q are independently oxygen or sulfur;

n is 0, 1 or 2;

X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbon atoms, trifluoromethyl, CH₃ S-- or CH₃ OCH₂ --; and

Y is methyl or methoxy; or their agriculturally suitable salts; provided that:

(a) when R₅ is other than hydrogen, at least one of R₃, R₄, R₆ and R₇ is other than hydrogen and at least two of R₃, R₄, R₆ and R₇ must be hydrogen;

(b) when R₅ is hydrogen and all of R₃, R₄, R₆ and R₇ are other than hydrogen, then all of R₃, R₄, R₆ and R₇ must be either chlorine or methyl; and

(c) when R₃ and R₇ are both hydrogen, at least one of R₄, R₅ or R₆ must be hydrogen.

In particular, the patent discloses ortho-substituted compounds wherein the substitution is C₁ -C₄ alkyl.

The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food needs, such as soybeans, corn, wheat and the like. The current population explosion and concomitant world food shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing the loss of a portion of valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency.

A wide variety of materials useful for killing, or inhbiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. However, the need exists for still more effective herbicides that destroy or retard weeds without causing significant damage to useful crops.

SUMMARY OF THE INVENTION

This invention relates to novel compounds of Formula I, agriculturally suitable compositions containing them, and their method of use as general as well as selective pre-emergence and post-emergence herbicides. ##STR5## where W is O or S;

Q is O or NR₅ ;

R₁ is C₁ -C₄ alkyl, C₁ -C₄ alkyl substituted with 1-3 atoms of F, Cl or Br, CH₂ CH₂ OCH₃, CH₂ CH₂ CH₂ OCH₃ or ##STR6## R₂ is H, F, Cl, Br, OCH₃, NO₂, CF₃ or C₁ -C₂ alkyl;

R₃ is H, F, Cl, Br or CH₃ ;

R₄ is H, CH₃ or OCH₃ ;

R₅ is C₁ -C₄ alkyl;

R₆ and R₇ are independently H, F, Cl, Br, CH₃, CF₃, NO₂ or OCH₃ ;

A is ##STR7## X is NH₂, N(CH₃)₂, NHCH₃, C₁ -C₄ alkyl, C₁ -C₄ alkyl substituted with 1-3 atoms of F, Cl or Br, CH₂ OCH₃, CH₂ OCH₂ CH₃, C₁ -C₄ alkoxy, C₁ -C₂ alkylthio, C₃ -C₄ alkenyloxy, C₃ -C₄ alkynyloxy, OCH₂ CH₂ OCH₃ or C₂ -C₄ alkoxy substituted with 1-3 atoms of F, Cl or Br;

n is 1 or 2;

Y is H, CH₃, OCH₃ or Cl;

X₁ is O or CH₂ ;

Y₁ is H, CH₃, OCH₃ or Cl;

X₂ and Y₂ are independently CH₃ or OCH₃ ; and

Z is CH, N, CCH₃, CBr, CCl, CF, CI, CC₂ H₅, CCH₂ CH₂ Cl or CCH₂ CH═CH₂ ;

provided that

(1) when Y is Cl, then Z is other than N and X is NH₂, NHCH₃, N(CH₃)₂, CH₃ or OCH₃ ;

(2) when Y is H, then X is OCH₃, CH₃ or CH₂ OCH₃, and Z is other than N;

(3) when W is S, then R₄ is H; and

(4) when R₄ is OCH₃, then Q is O.

Preferred for reasons of higher herbicidal activity and/or more favorable ease of synthesis are:

(1) Compounds of the generic scope where R₅ is CH₃, W is O, and R₄ is H or CH₃ ;

(2) Compounds of Preferred (1) where R₁ is C₁ -C₄ alkyl, CF₃, CH₂ CH₂ OCH₃ or CH₂ CH₂ CH₂ OCH₃ ;

(3) Compounds of Preferred (2) where R₂ is H or Cl;

(4) Compounds of Preferred (3) where R₃ is H;

(5) Compounds of Preferred (4) where

R₁ is C₁ -C₃ alkyl or CF₃ ;

Q is O;

A is ##STR8## and Z is CH or N;

(6) Compounds of Preferred (5) where R₄ is H;

(7) Compounds of Preferred (6) where X and Y are independently CH₃ or OCH₃, and R₁ is CH₃ ; and

(8) Compounds of the generic scope where

Q is ##STR9## R₅ is CH₃ or CH₃ CH₂ ; R₁ is C₁ -C₃ alkyl or CF₃ ;

R₂ and R₃ are H;

X is CH₃, OCH₃, N(CH₃), CH₂ OCH₃, OCH₂ CH₃ or OCH₂ CF₃ ;

Y is CH₃, OCH₃ or Cl; and

Z is CH or N.

Specifically preferred for highest herbicidal activity and/or most favorable ease of synthesis are:

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-hydroxy-5-chlorobenzenesulfonamide methanesulfonate;

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-hydroxybenzenesulfonamide, methanesulfonate;

2-hydroxy-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide, methanesulfonate; and

N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-hydroxybenzenesulfonamide, methanesulfonate.

All of the above compounds show selectivity on wheat.

N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-hydroxybenzenesulfonamide, methanesulfonate;

2-hydroxy-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide, methanesulfonate;

N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-hydroxybenzenesulfonamide, methanesulfonate;

N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)(methyl)aminocarbonyl]-2-hydroxybenzenesulfonamide, methanesulfonate;

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-hydroxybenzenesulfonamide, 1-propanesulfonate, which shows selectively on rice and corn; and

2-hydroxy-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide, 1-propanesulfonate, which shows selectivity on soybeans.

This invention also relates to compounds of Formula II which are useful intermediates for the preparation of the herbicidal compounds of Formula I: ##STR10## where W is O or S;

Q is O or NR₅ ;

R₁ is C₁ -C₄ alkyl, C₁ -C₄ alkyl substituted with 1-3 atoms of F, Cl or Br, CH₂ CH₂ OCH₃, CH₂ CH₂ CH₂ OCH₃, or ##STR11## R₂ is H, F, Cl, Br, OCH₃, NO₂ or C₁ -C₂ alkyl; R₃ is H, F, Cl, Br or CH₃ ;

R₅ is C₁ -C₄ alkyl; and

R₆ and R₇ are independently H, F, Cl, Br, CH₃, CF₃, NO₂ or OCH₃.

Preferred intermediates, for reasons of more favorable ease of synthesis and/or higher herbicidal activity of the compounds of Formula I, are:

(1) Compounds of Formula II where Q is O, R₂ and R₃ are H, R₁ is CH₃ or CF₃, and W is O.

This invention also relates to compunds of Formula VII which are useful intermediates for the preparation of the herbicidal compounds of Formula I: ##STR12## where Q is O or NR₅ ;

R₁ is C₁ -C₄ alkyl, C₁ -C₄ alkyl substituted with 1-3 atoms of F, Cl or Br, CH₂ CH₂ OCH₃, CH₂ CH₂ CH₂ OCH₃, or ##STR13## R₂ is H, F, Cl, Br, OCH₃, NO₂ or C₁ -C₂ alkyl; R₃ is H, F, Cl, Br or OCH₃ ;

R₅ is C₁ -C₄ alkyl;

R₆ and R₇ are independently H, F, Cl, Br, CH₃, CF₃, NO₂ or OCH₃ ; and

Z is CH or N.

SYNTHESIS

The compounds of this invention can be made as outlined below. The compounds of Formula (IV), (VI), (XII) or (XIV) in which Q is oxygen can be prepared by reacting an appropriate 2-aminopyrimidine, 2-aminotriazine or 2-aminobicyclopyrimidine of Formula (III), (V), (XI) or (XIII) with an appropriately substituted sulfonylisocyanate or isothiocyanate, of Formula (II), where Q is oxygen and R₁, R₂, R₃, R₄, X, Y, Z, X₁, X₂, Y₁, Y₂, W and n are as previously defined.

The reaction is best carried out in inert solvents such as methylene chloride and acetonitrile. The mode of addition is not critical, however, it is often convenient to add a solution of the isocyanate or isothiocyanate of Formula (II) to a stirred suspension of the aminoheterocycle (III), (V), (XI) or (XIII).

The reaction is generally exothermic. In some cases, the desired product is insoluble in the reaction medium and crystallizes from it in pure form. Products soluble in the reaction medium are isolated by evaporation of the solvent and trituration of the residue with solvents such as diethyl ether, 1-chlorobutane, or hexanes and filtration. ##STR14##

Some of the compounds of this invention, where Z is CH or N, may also be prepared by reacting a sulfonamide of Formula VIII with a 4,6-dichloroheterocyclic isocyanate of Formula IX. ##STR15##

One or both of the halogen atoms on the heterocyclic ring of the compound of Formula VII can be displaced by an alkoxide of OR₈, to give compounds of Formula X, where R₈ is C₁ -C₄ alkyl, C₃ -C₄ alkenyl, C₃ -C₄ alkynyl, CH₂ CH₂ OCH₃ or C₂ -C₄ alkyl substituted with 1-3 atoms of F, Cl or Br, and Y" is Cl or OCH₃. ##STR16##

The process for the preparation of compounds of Formula X is described in our patent application Ser. No. 193,190, filed Oct. 14, 1980.

Compounds of Formula IV, VI, XII and XIV in which Q is ##STR17## are best prepared by the procedure of Equation 5 wherein R₁, R₂, R₃, R₄, R₅ and A are as previously defined. ##STR18##

The reaction of Equation 5 is best carried out in methylene chloride at 25° to 40° C. for 24 to 96 hours under a nitrogen atmosphere. The product can be isolated by the addition of an aqueous acetic acid solution followed by extraction of the product into methylene chloride or direct filtration of a product of low solubility. The product can ordinarily be purified by trituration with solvents such as n-butyl chloride or ether or by column chromatography.

Further details of this reaction and the preparation of the carbamates of Formula III can be found in unexamined European Patent Application 174-73.

Sulfonamides of Formula VIII in which Q is ##STR19## are readily prepared as shown by Equations 6 and 7. ##STR20## M is an alkali metal.

The reaction of Equation 6 is carried out in an aprotic solvent such as dimethylformamide at temperatures ranging from about ambient to reflux for periods ranging from 1/4 to 24 hours.

The product is isolated by removing the solvent at reduced pressure and pouring the reaction mixture into H₂ O. The crude product is extracted with an organic solvent such as methylene chloride. The solution of the product is dried with a standard drying agent such as MgSO₄, filtered, and concentrated. The crude product is further purified by usual techniques such as recrystallization or chromatography.

The reduction of the nitro compounds such as XIX to anilines XX is achieved by procedures well known to those skilled in the art.

Anilines of Formula XX are converted to sulfonyl chlorides by well known procedures. For further details, see H. L. Yale and F. Sowinski, J. Org. Chem., 25, 1824 (1960).

Sulfonamides of Formula VIII in which Q is ##STR21## are obtained by treatment of sulfonyl chlorides of Formula XXI with NH₃ by procedures known to those skilled in the art.

Sulfonamides of Formula VIII in which Q is oxygen, prepared as described in Research Disclosure, pg. 52, (1978), may conveniently be converted to the corresponding isocyanates or isothiocyanates of Formula II by methods described in U.S. Pat. No. 4,127,405.

The synthesis of the heterocyclicamine derivatives has been reviewed in "The Chemistry of Heterocyclic Compounds", a series published in Interscience Publ., New York and London.

2-Aminopyrimidines are described by D. J. Brown in "The Pyrimidines", Vol. XVI of the above series which are herein incorporated by reference.

The preparation of amino bicyclopyrimidines are described in unexamined European Pat. No. 15683.

The aminoheterocyclic intermediates of Formula III, V, XI or XIII in which R₄ is CH₃, may be prepared by the following procedure, or by obvious modifications thereof. ##STR22##

A solution of the amine XV in concentrated hydrochloric acid is contacted with an aqueous sodium nitrite solution and the chloro compound XVI is isolated by filtration of the acidic solution (see for example, Bee and Rose, J. Chem. Soc. C., 2051 (1966) for the case in which Z is CH and X and Y are OCH₃). Displacement of the chlorine may be accomplished by heating with an excess of methylamine in water to obtain the methylaminoheterocycle XXIV.

N-Methoxyamino heterocycles can be prepared by procedures reported in the literature [see, for example, Belgian Patent 618,563 and J. T. Shaw, et al., J. Org. Chem., 27 4054 (1962)] and the procedure illustrated below. ##STR23##

Chloro compound XXIII is reacted with hydroxylamine to form derivative XXV which may be alkylated with methyl bromide to afford the N-methoxy heterocyclic amine XXVI. This compound may alternately be prepared in one step by treatment of XXIII and O-methyl hydroxylamine hydrochloride with an alkali metal hydroxide such as sodium hydroxide.

The compounds of this invention and their preparation are further illustrated by the following examples, wherein temperatures are given in degrees centigrade and parts are by weight unless otherwise indicated.

EXAMPLE 1 2-Hydroxybenzenesulfonyl isocyanate, methanesulfonate

To 10.0 g (0.04 mole) 2-hydroxybenzenesulfonamide, methanesulfonate, suspended in 75 ml dry xylenes was added 4.0 g (0.04 mole) N-butylisocyanate and a catalytic amount of 1,4-diazobicyclo[2.2.2]octane (˜0.05 g). This mixture was rapidly heated to reflux temperature (˜135° C.) and 4.0 ml of phosgene was slowly added (at such a rate to keep the reaction temperature greater tha 128° C.). The phosgene addition required ˜11/2 hours. The reaction was cooled to room temperature, filtered under N₂, and the solvent evaporated under reduced pressure. The infrared spectrum of the resultant oil was consistent for 2-hydroxybenzenesulfonyl isocyanate, methanesulfonate (2210 cm⁻¹).

EXAMPLE 2 N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-hydroxybenzenesulfonamide, methanesulfonate

To a suspension of 0.06 g 2-amino-4,6-dimethoxypyrimidine in 10 ml dry methylene chloride is added 1.1 g 2-hydroxybenzenesulfonylisocyanate, methanesulfonate. The reaction exotherms (21° C.-29° C.) and is then stirred 1/2 hour. The solvent is evaporated under reduced pressure. The resultant mixture is triturated with diethylether and filtered to give 1.2 g tan solid m.p. 165°-166° C. The infrared spectrum shows absorption bands at 1740, 1615, 1590, 1360 cm⁻¹.

Calc. for C--38.9, H--3.73, N--12.9. Found C--38.3, H--3.63, N--13.0.

EXAMPLE 3 2-Hydroxy-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide, methanesulfonate

To a suspension of 0.6 g 2-amino-4-methoxy-6-methylpyrimidine in 10 ml dry methylene chloride is added 1.1 g 2-hydroxybenzenesulfonylisocyanate, methanesulfonate. The reaction exotherms mildly and is then stirred for 1/2 hour. The solvent is evaporated under reduced pressure. The resultant mixture is triturated with diethylether and filtered to give 0.95 g white solid m.p. 189°-190° C. The infrared spectrum shows absorption bands at 1700, 1615, 1560, 1370 cm⁻¹.

Calc. for C--40.4, H--3.87, N--13.4. Found C--40.2, H--3.77, N--13.6.

EXAAMPLE 4 N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-hydroxybenzenesulfonate, methanesulfonate

To a suspension of 0.6 g 2-amino-4,6-dimethoxy-1,3,5-triazine in 10 ml dry methylene chloride is added 1.1 g 2-hydroxybenzenesulfonylisocyanate, methanesulfonate. The reaction exotherms mildly and is then stirred for about 1 hour. The solvent is evaporated under reduced pressure. The resultant mixture is triturated with diethylether and filtered to give 1.4 g tan solid m.p. 163°-166° C. The infrared spectrum shows absorption bands at 1715, 1600, 1550, 1350 cm⁻¹.

EXAMPLE 5 Preparation of N-methyl-N-(2-nitrophenyl)methanesulfonamide

To 3.2 g of N-methyl methanesulfonamide in 50 ml of dry dimethylformamide is added 1.47 g of potassium methoxide. The mixture is stirred for 15 minutes. 2.8 g of 2-Fluoronitrobenzene is added and the mixture is heated to reflux for two hours. The dimethylformamide is removed on a rotary evaporator. The concentrated reaction mixture is poured into water. The crude product is extracted with CH₂ Cl₂. The crude extracts are dried with MgSO₄, filtered and concentrated on a rotary evaporator. The crude product is purified by recrystallization from butyl chloride-ethyl acetate. 3.4 g of product with m.p. 144°-145° C. is obtained.

EXAMPLE 6 N-(2-Aminophenyl)-N-methyl methanesulfonamide

50.2 g of N-methyl-N-(2-nitrophenyl)methanesulfonamide, prepared by the procedure of Example 5, is added to 220 ml of concentrated HCl and contacted with 183.3 g of SnCl₂.2H₂ O. The mixture is heated on a steam bath for one hour. The reaction mixture is treated with enough 5-10% NaOH to raise the pH to 9 while maintaining the temperature of the mixture less than 25° C. The crude reaction mixture is then extracted with CH₂ Cl₂. The CH₂ Cl₂ extracts are dried with MgSO₄ and then filtered and concentrated on a rotary evaporator. The solid product obtained (38.1 g), m.p. 138°-139° was used without further purification in the next step.

EXAMPLE 7 2-[N-methyl-N-(methylsulfonyl)amino]benzenesulfonamide Diazotization

20.0 g of amine from Example 6 is combined with 50 ml of acetic acid, 30 ml of H₂ O and 39.4 g of concentrated aqueous hydrochloric acid; the mixture is cooled to 0°-5° C. A solution of 7.2 g of NaNO₂ in 20 ml of H₂ O is added dropwise over a period of 15-30 minutes, while maintaining the temperature. The reaction mixture is stirred for 30 minutes at 0°-10° C. and then used in the subsequent coupling step.

Coupling

The diazonium salt from the preceding step is added dropwise over 15-30 minutes to a solution of 22.3 ml SO₂, 350 ml of acetic acid and 1.35 g of CuCl cooled to 12°-15° C. After the addition is completed the reaction is stirred at 10°-15° C. for one hour. The cooling bath was removed and the reaction mixture was stirred at ambient temperature for 12 hours. The crude reaction mixture was then poured into water and extracted with ether. The ether extract was back-extracted with H₂ O and then dried with MgSO₄, filtered and concentrated to the wet solid sulfonyl chloride which was used in the next step without further purification.

Amination

The crude product from the preceding step was taken up in 175 ml of tetrahydrofuran and cooled to 0°-5° C. 75 ml of concentrated aqueous ammonia was added dropwise while maintaining the temperature. The reaction mixture was allowed to warm to ambient temperature over a period of one hour. The crude reaction mixture was poured into water. The crude product was extracted with CH₂ Cl₂, dried with MgSO₄, filtered and concentrated on a rotary evaparator. 10.8 g of product with m.p. 137°-139° was obtained and used in the next step without further purification.

EXAMPLE 8 N-[(4,6-dimethoxypyrimidin-2-yl)]-2-[(methyl)(methylsulfonyl)amino]benzenesulfonamide

1.5 g of sulfonamide from Example 8 is added to 60 ml of dry methylene chloride under N₂. 3.6 ml of 2M solution of (CH₃)₃ Al in hexane was added. The mixture was stirred for 15 minutes and 1.2 g of ##STR24## was added. The mixture was refluxed for 16 hours. 50 ml of H₂ O was added dropwise cautiously followed by enough acetic acid to lower the pH of the reaction mixture to 2-3. The crude product is then extracted with CH₂ Cl₂, dried with MgSO₄, filtered and concentrated on a rotary evaporator. The crude solid product was triturated with butyl chloride-ethyl acetate. 1.2 g of product with m.p. 228°-230° was obtained.

Using the procedures similar to those of Examples 1-8, the following compounds can be prepared.

                                      TABLE I                                      __________________________________________________________________________      ##STR25##                                                                     R.sub.1     R.sub.2                                                                              R.sub.3                                                                            R.sub.4                                                                            Q      W Y   X        Z        m.p.                  __________________________________________________________________________                                                              (°C.)          CH.sub.3    H     H   H   O      O OCH.sub.3                                                                          OCH.sub.3                                                                               CH       165-166               CH.sub.3    H     H   H   O      O OCH.sub.3                                                                          CH.sub.3 CH       189-190               CH.sub.3    H     H   H   O      O CH.sub.3                                                                           CH.sub.3 CH       204-205               CH.sub.3    H     H   H   O      O OCH.sub.3                                                                          OCH.sub.3                                                                               N        163-166               CH.sub.3    H     H   H   O      O OCH.sub.3                                                                          CH.sub.3 N        170-173               CH.sub.3    H     H   H   O      O CH.sub.3                                                                           CH.sub.3 N        181-184               (CH.sub. 2).sub.3 CH.sub.3                                                                 H     H   H   O      O OCH.sub.3                                                                          OCH.sub.3                                                                               CH       158-162               (CH.sub.2).sub.2 CH.sub.2 Cl                                                               H     H   H   O      O OCH.sub.3                                                                          OCH.sub.3                                                                               CH                             CCl.sub.3   H     H   H   O      O OCH.sub.3                                                                          OCH.sub.3                                                                               CH                              ##STR26##  H     H   H   O      O OCH.sub.3                                                                          CH.sub.3 CH       216-219                ##STR27##  H     H   H   O      O OCH.sub.3                                                                          CH.sub.3 CH                              ##STR28##  H     H   H   O      O OCH.sub.3                                                                          CH.sub.3 CH                              ##STR29##  H     H   H   O      O OCH.sub.3                                                                          CH.sub.3 CH                              ##STR30##  H     H   H   O      O OCH.sub.3                                                                          CH.sub.3 CH                              ##STR31##  H     H   H   O      O OCH.sub.3                                                                          CH.sub.3 CH                              ##STR32##  H     H   H   O      O OCH.sub.3                                                                          CH.sub.3 CH                              ##STR33##  H     H   H   O      O OCH.sub.3                                                                          CH.sub.3 CH                              ##STR34##  H     H   H   O      O OCH.sub.3                                                                          CH.sub.3 CH                             CH.sub.3    5-Cl  H   H   O      O OCH.sub.3                                                                          OCH.sub.3                                                                               CH       174-176               CH.sub.3    6-CH.sub.3                                                                           H   H   O      O OCH.sub.3                                                                          CH.sub.3 CH                             CH.sub.3    5-F   H   H   O      O OCH.sub.3                                                                          CH.sub.3 CH                             CH.sub.3    5-NO.sub.2                                                                           H   H   O      O OCH.sub.3                                                                          CH.sub.3 CH                             CH.sub.3    5-Br  H   H   O      O OCH.sub.3                                                                          CH.sub.3 CH                             CH.sub.3    5-OCH.sub.3                                                                          H   H   O      O OCH.sub.3                                                                          CH.sub.3 CH                             CH.sub.3    5-CF.sub.3                                                                           H   H   O      O OCH.sub.3                                                                          CH.sub.3 CH                             CH.sub.3    5-Cl  4-Cl                                                                               H   O      O OCH.sub.3                                                                          CH.sub.3 CH                             CH.sub.3    5-CH.sub.3                                                                           4-CH.sub.3                                                                         H   O      O OCH.sub.3                                                                          CH.sub.3 CH                             CH.sub.3    H     H   CH.sub.3                                                                           O      O OCH.sub.3                                                                          OCH.sub.3                                                                               N        91-96                 CH.sub.3    H     H   H   NCH.sub.3                                                                             O OCH.sub.3                                                                          OCH.sub.3                                                                               CH       228-230               CH.sub.3    H     H   H                                                                                   ##STR35##                                                                            O OCH.sub.3                                                                          OCH.sub.3                                                                               CH                             CH.sub.3    H     H   H   O      O Cl  OCH.sub.3                                                                               CH                             CH.sub.3    H     H   H   O      O OCH.sub.3                                                                          (CH.sub.2).sub.3 CH.sub.3                                                               CH                             CH.sub.3    H     H   H   O      O CH.sub.3                                                                           OCH.sub.2 CF.sub.3                                                                      N                              CH.sub.3    H     H   H   O      O CH.sub.3                                                                           OCH.sub.2 CCl.sub.3                                                                     N                              CH.sub.3    H     H   H   O      O CH.sub.3                                                                           OCH.sub.2 CBr.sub.3                                                                     N                              CH.sub.3    H     H   H   O      O CH.sub.3                                                                           OCH.sub.2 CH.sub.2 Cl                                                                   N                              CH.sub.3    H     H   H   O      O CH.sub.3                                                                           H        CH                             CH.sub.3    H     H   H   O      O CH.sub.3                                                                           (CH.sub.2).sub.3 CH.sub.3                                                               CH                             CH.sub.3    H     H   H   O      O CH.sub.3                                                                           CH.sub.2 CH.sub.2 Cl                                                                    CH                             CH.sub.3    H     H   H   O      O CH.sub.3                                                                           CH.sub.2 CF.sub.3                                                                       CH                             CH.sub.3    H     H   H   O      O CH.sub. 3                                                                          O(CH.sub.2).sub.3 CH.sub.3                                                              N                              CH.sub.3    H     H   H   O      O CH.sub.3                                                                           OCH.sub.2 CHCH.sub.2                                                                    N                              CH.sub.3    H     H   H   O      O CH.sub.3                                                                            ##STR36##                                                                              N                              CH.sub.3    H     H   H   O      O CH.sub.3                                                                           OCH.sub.2 CCH                                                                           N                              CH.sub.3    H     H   H   O      O CH.sub.3                                                                           OCH.sub.2 CCCH.sub.3                                                                    N                              CH.sub.3    H     H   H   O      O CH.sub.3                                                                           CH.sub.2 OCH.sub.3                                                                      CH                             CH.sub.3    H     H   H   O      O CH.sub.3                                                                           SCH.sub.3                                                                               CH                             CH.sub.3    H     H   H   O      O CH.sub.3                                                                           S(CH.sub.2)CH.sub.3                                                                     CH                             CH.sub.3    H     H   H   O      O CH.sub.3                                                                           CH.sub.3 CBr                            CH.sub.3    H     H   H   O      O CH.sub.3                                                                           CH.sub.3 CI                             CH.sub.3    H     H   H   O      O CH.sub.3                                                                           CH.sub.3 CF                             CH.sub.3    H     H   H   O      O CH.sub.3                                                                           CH.sub.3 CCl                            CH.sub.3    H     H   H   O      S OCH.sub.3                                                                          OCH.sub.3                                                                               N                              CH.sub.3    H     H   H   O      S OCH.sub.3                                                                          CH.sub.3 N                              CH.sub.3    H     H   H   O      S CH.sub.3                                                                           CH.sub.3 N                              CH.sub.3    H     H   H   O      S OCH.sub.3                                                                          CH.sub.3 CH                             CH.sub.3    H     H   H   O      S OCH.sub.3                                                                          OCH.sub.3                                                                               CH                             CH.sub.3    H     H   H   O      S CH.sub.3                                                                           CH.sub.3 CH                             CH.sub.3    3-Cl  H   H   O      O OCH.sub.3                                                                          OCH.sub.3                                                                               CH       134-142               CH.sub.3    3-Cl  H   H   O      O OCH.sub.3                                                                          OCH.sub.3                                                                               N        165-170               CH.sub.3    3-Cl  5-Cl                                                                               H   O      O OCH.sub.3                                                                          CH.sub.3 N        210 (dec)             CH.sub.3    3-Cl  5-Cl                                                                               H   O      O OCH.sub.3                                                                          OCH.sub.3                                                                               N        200 (dec)             CH.sub.3    H     H   H   NCH.sub.2 CH.sub.3                                                                    O OCH.sub.3                                                                          OCH.sub.3                                                                               CH                             CH.sub.3    H     H   H   N(CH.sub.2).sub.2 CH.sub.3                                                            O OCH.sub.3                                                                          OCH.sub.3                                                                               CH                             CH.sub.3    H     H   H   NCH.sub.3                                                                             O OCH.sub.3                                                                          CH.sub.3 CH       220-222               CH.sub.3    H     H   H   NCH.sub.3                                                                             O CH.sub.3                                                                           CH.sub.3 CH       216-218               CH.sub.3    H     H   H   NCH.sub.3                                                                             O OCH.sub.3                                                                          CH.sub.3 N        218-221 (d)           CH.sub.2 CH.sub.3                                                                          H     H   H   O      O OCH.sub. 3                                                                         OCH.sub.3                                                                               CH       189-191               CH.sub.2 CH.sub.3                                                                          H     H   H   O      O OCH.sub.3                                                                          CH.sub.3 CH       160-162               CH.sub.2 CH.sub.3                                                                          H     H   H   O      O CH.sub.3                                                                           CH.sub.3 CH       196-198               CH.sub.2 CH.sub.3                                                                          H     H   H   O      O OCH.sub.3                                                                          OCH.sub.3                                                                               N                              CH.sub.2 CH.sub.3                                                                          H     H   H   O      O OCH.sub.3                                                                          CH.sub.3 N                              CH.sub.2 CH.sub.3                                                                          H     H   H   O      O CH.sub.3                                                                           CH.sub.3 N                              CH.sub.2 CH.sub.3                                                                          H     H   CH.sub.3                                                                           O      O OCH.sub.3                                                                          OCH.sub.3                                                                               N                              (CH.sub.2).sub.3 CH.sub.3                                                                  H     H   H   O      O OCH.sub.3                                                                          CH.sub.3 CH                             (CH.sub.2).sub.3 CH.sub.3                                                                  H     H   H   O      O CH.sub.3                                                                           CH.sub.3 CH       201-202               (CH.sub.2).sub.3 CH.sub.3                                                                  H     H   H   O      O OCH.sub.3                                                                          OCH.sub.3                                                                               N        150-153               (CH.sub.2).sub.3 CH.sub.3                                                                  H     H   H   O      O OCH.sub.3                                                                          CH.sub.3 N        161-163               (CH.sub.2).sub.3 CH.sub.3                                                                  H     H   H   O      O CH.sub.3                                                                           CH.sub.3 N                              (CH.sub.2).sub.3 CH.sub.3                                                                  H     H   H   O      O H   CH.sub.3 CCl      135-140               (CH.sub.2 ).sub.2 CH.sub.3                                                                 H     H   H   O      O OCH.sub.3                                                                          OCH.sub.3                                                                               CH       172-174               (CH.sub.2).sub.2 CH.sub.3                                                                  H     H   H   O      O OCH.sub.3                                                                          CH.sub.3 CH       183-186               (CH.sub.2).sub.2 CH.sub.3                                                                  H     H   H   O      O CH.sub.3                                                                           CH.sub.3 CH       182-184               (CH.sub.2).sub.2 CH.sub.3                                                                  H     H   H   O      O OCH.sub.3                                                                          OCH.sub.3                                                                               N        151-154               (CH.sub.2).sub.2 CH.sub.3                                                                  H     H   H   O      O OCH.sub.3                                                                          CH.sub.3 N        144-147               (CH.sub.2).sub.2 CH.sub.3                                                                  H     H   H   O      O CH.sub.3                                                                           CH.sub.3 N                              (CH.sub.2).sub.2 CH.sub.3                                                                  H     H   CH.sub.3                                                                           O      O OCH.sub.3                                                                          OCH.sub.3                                                                               CH                             (CH.sub.2).sub.2 CH.sub.3                                                                  H     H   H   O      O H   CH.sub.3 CCl      185-190               CF.sub.3    H     H   H   O      O OCH.sub.3                                                                          OCH.sub.3                                                                               CH       129-131               CH.sub.2 CH.sub.2 Br                                                                       H     H   H   O      O OCH.sub.3                                                                          OCH.sub.3                                                                               CH                             CH.sub.2 CH.sub.2 OCH.sub.3                                                                H     H   H   O      O OCH.sub.3                                                                          OCH.sub.3                                                                               CH                             CH.sub.2 CH.sub.2 OCH.sub.3                                                                H     H   H   O      O OCH.sub.3                                                                          CH.sub.3 CH                             CH.sub. 2 CH.sub.2 OCH.sub.3                                                               H     H   H   O      O CH.sub.3                                                                           CH.sub.3 N                              CH.sub.2 CH.sub.2 OCH.sub.3                                                                H     H   H   O      O OCH.sub.3                                                                          CH.sub.3 N                              (CH.sub.2).sub.2 CH.sub.2 OCH.sub.3                                                        H     H   H   O      O OCH.sub.3                                                                          OCH.sub.3                                                                               CH                             CH.sub.3    H     H   H   O      O Cl  NH.sub.2 CH                             CH.sub.3    H     H   H   O      O Cl  NHCH.sub.3                                                                              CH                             CH.sub.3    H     H   H   O      O Cl  N(CH.sub.3).sub.2                                                                       CH                             CH.sub.3    H     H   H   O      O CH.sub.3                                                                           CH.sub.2 OCH.sub.3                                                                      CH                             CH.sub.2 CH.sub.3                                                                          H     H   H   O      O CH.sub.3                                                                           CH.sub.2 OCH.sub.3                                                                      CH                             (CH.sub.2).sub.2 CH.sub.3                                                                  H     H   H   O      O CH.sub.3                                                                           CH.sub.2 OCH.sub.3                                                                      CH                             CH.sub.3    H     H   H   O      O CH.sub.3                                                                           CH.sub.2 OCH.sub.2 CH.sub.3                                                             CH                             CH.sub.3    H     H   H   O      O CH.sub.3                                                                           CH.sub.2 CH.sub.3                                                                       CH                             CH.sub.3    H     H   H   O      O CH.sub.3                                                                           CH.sub.2 CH.sub.2 CH.sub.3                                                              CH                             CH.sub.3    H     H   H   O      O CH.sub.3                                                                           CH.sub.2 CH.sub.2 Br                                                                    CH                             CH.sub.3    H     H   H   O      O CH.sub.3                                                                           OCH.sub.2 CH.sub.3                                                                      CH                             CH.sub.3    H     H   H   O      O CH.sub.3                                                                           O(CH.sub.2).sub.2 CH.sub.3                                                              CH                             CH.sub.3    H     H   H   O      O CH.sub.3                                                                           OCH.sub.2 CHCH.sub.2                                                                    CH                             CH.sub.3    H     H   H   O      O CH.sub.3                                                                            ##STR37##                                                                              CH                             CH.sub.3    H     H   H   O      O CH.sub.3                                                                           OCH.sub.2 CCH                                                                           CH                             CH.sub.3    H     H   H   O      O CH.sub.3                                                                           OCH.sub.2 CCCH.sub.3                                                                    CH                             CH.sub.3    H     H   H   O      O CH.sub.3                                                                           OCH.sub.2 CH.sub.2 OCH.sub.3                                                            CH                             CH.sub.3    H     H   H   O      O CH.sub.3                                                                           OCH.sub.2 CH.sub.2 OCH.sub.3                                                            N                              CH.sub.3    H     H   H   O      O CH.sub.3                                                                           OCH.sub.2 (CH.sub.2).sub.2                                                              CH                             CH.sub.3    H     H   H   O      O CH.sub.3                                                                           OCH.sub.2 (CH.sub.2).sub.3                                                              CH                             CH.sub.3    H     H   H   O      O H   CH.sub.3 CCl                            CH.sub.3    H     H   H   O      O Cl  CH.sub.3 CCH.sub.2 CH.sub.2 Cl          CH.sub. 3   H     H   H   O      O OCH.sub.3                                                                          OCH.sub.3                                                                               CH.sub.3                       CH.sub.3    H     H   H   O      O OCH.sub.3                                                                          OCH.sub.3                                                                               CH.sub.2 CH.sub.3              CH.sub.3    H     H   H   O      O OCH.sub.3                                                                          OCH.sub.3                                                                               CCH.sub.2 CHCH.sub.2           CH.sub.3    5-Cl  H   H   O      O OCH.sub.3                                                                          CH.sub.3 CH       179-181               CH.sub.3    5-Cl  H   H   O      O CH.sub.3                                                                           CH.sub.3 CH       204-205               CH.sub.3    5-Cl  H   H   O      O OCH.sub.3                                                                          OCH.sub.3                                                                               N        180-186               CH.sub.3    5-Cl  H   H   O      O OCH.sub.3                                                                          CH.sub.3 N        184-187               CH.sub.3    5-Cl  H   H   O      O H   CH.sub.3 CCl      210-211               CH.sub.3    5-CH.sub.3                                                                           H   H   O      O OCH.sub.3                                                                          OCH.sub.3                                                                               CH       171-174               CH.sub.3    5-CH.sub.3                                                                           H   H   O      O OCH.sub.3                                                                          CH.sub.3 CH       181-188               CH.sub.3    5-CH.sub.3                                                                           H   H   O      O CH.sub.3                                                                           CH.sub.3 CH       180-183               CH.sub.3    5-CH.sub.3                                                                           H   H   O      O OCH.sub.3                                                                          CH.sub.3 N        159-161               CH.sub.3    5-CH.sub.3                                                                           H   H   O      O OCH.sub.3                                                                          OCH.sub.3                                                                               N        178-181               CH.sub.3    5-CH.sub.3                                                                           H   H   O      O CH.sub.3                                                                           CH.sub.3 N                              CH.sub.3    5-CH.sub.3                                                                           H   CH.sub.3                                                                           O      O OCH.sub.3                                                                          OCH.sub.3                                                                               N        133-136               CH.sub.3    5-CH.sub.2 CH.sub.3                                                                  H   H   O      O OCH.sub.3                                                                          CH.sub.3 CH                              ##STR38##  H     H   H   O      O OCH.sub.3                                                                          OCH.sub.3                                                                               CH       221-223                ##STR39##  H     H   H   O      O CH.sub.3                                                                           CH.sub.3 CH       182-186                ##STR40##  H     H   H   O      O OCH.sub.3                                                                          CH.sub.3 N        184-186                ##STR41##  H     H   H   O      O OCH.sub.3                                                                          OCH.sub.3                                                                               N        169-172                ##STR42##  H     H   H   O      O CH.sub.3                                                                           CH.sub.3 N                               ##STR43##  H     H   H   O      O H   CH.sub.3 CCl      193-195                ##STR44##  H     H   CH.sub.3                                                                           O      O OCH.sub.3                                                                          OCH.sub.3                                                                               N        143-145               CH.sub.3    H     H   OCH.sub.3                                                                          O      O OCH.sub.3                                                                          OCH.sub.3                                                                               CH                              ##STR45##  H     H   H   O      O OCH.sub.3                                                                          OCH.sub.3                                                                               CH                             CF.sub.3    H     H   H   O      O OCH.sub.3                                                                          CH.sub.3 CH       135-140 (d)           CF.sub.3    H     H   H   O      O CH.sub.3                                                                           CH.sub.3 CH       190-193 (d)           CF.sub.3    H     H   H   O      O OCH.sub.3                                                                          OCH.sub.3                                                                               N                              CF.sub.3    H     H   H   O      O OCH.sub.3                                                                          CH.sub.3 N                              CF.sub.3    H     H   H   O      O CH.sub.3                                                                           CH.sub.3 N        200 (d)               CF.sub.3    H     H   CH.sub.3                                                                           O      O OCH.sub.3                                                                          OCH.sub.3                                                                               N        144-148 (d)           CF.sub.3    H     H   H                                                                                   ##STR46##                                                                            O OCH.sub.3                                                                          OCH.sub.3                                                                               CH       195-197               CF.sub.3    H     H   H                                                                                   ##STR47##                                                                            O OCH.sub.3                                                                          CH.sub.3 CH       199-200               CF.sub.3    H     H   H                                                                                   ##STR48##                                                                            O CH.sub.3                                                                           CH.sub.3 CH       221-224               CF.sub.3    H     H   H                                                                                   ##STR49##                                                                            O OCH.sub.3                                                                          OCH.sub.3                                                                               N        151-154               CF.sub.3    H     H   H                                                                                   ##STR50##                                                                            O OCH.sub.3                                                                          CH.sub.3 N        180-182               CF.sub. 3   H     H   H                                                                                   ##STR51##                                                                            O CH.sub.3                                                                           CH.sub.3 N        200-201               CF.sub.3    H     H   CH.sub.3                                                                            ##STR52##                                                                            O OCH.sub.3                                                                          OCH.sub.3                                                                               N                              CH.sub.2 CH.sub.3                                                                          H     H   H   O      O Cl  OCH.sub.3                                                                               CH                             CH.sub.2 CH.sub.2 CH.sub.3                                                                 H     H   H   O      O Cl  OCH.sub.3                                                                               CH                             CH.sub.3    H     H   H   O      O OCH.sub.3                                                                          N(CH.sub.3).sub.2                                                                       CH                             CH.sub.2 CH.sub.3                                                                          H     H   H   O      O OCH.sub.3                                                                          N(CH.sub.3).sub.2                                                                       N                              CH.sub.2 CH.sub.2 CH.sub.3                                                                 H     H   H   O      O OCH.sub.3                                                                          N(CH.sub.3).sub.2                                                                       CH                             CH.sub.2 CH.sub.3                                                                          H     H   H   O      O Cl  N(CH.sub.3).sub.2                                                                       CH                             CH.sub.2 CH.sub.2 CH.sub.3                                                                 H     H   H   O      O Cl  N(CH.sub.3).sub.2                                                                       CH                             CH.sub.3    H     H   H                                                                                   ##STR53##                                                                            O Cl  OCH.sub.3                                                                               CH                             CF.sub.3    H     H   H                                                                                   ##STR54##                                                                            O Cl  OCH.sub.3                                                                               CH                             CH.sub.3    H     H   H                                                                                   ##STR55##                                                                            O OCH.sub.3                                                                          N(CH.sub.3).sub.2                                                                       CH                             CF.sub.3    H     H   H                                                                                   ##STR56##                                                                            O OCH.sub.3                                                                          N(CH.sub.3).sub.2                                                                       N                              CH.sub.3    H     H   H                                                                                   ##STR57##                                                                            O Cl  N(CH.sub.3).sub.2                                                                       CH                             CF.sub.3    H     H   H                                                                                   ##STR58##                                                                            O Cl  N(CH.sub.3).sub.2                                                                       CH                             CH.sub.3    H     H   H                                                                                   ##STR59##                                                                            O CH.sub.3                                                                           CH.sub.3 N        212-213               CH.sub.3    H     H   H                                                                                   ##STR60##                                                                            O OCH.sub.3                                                                          OCH.sub.3                                                                               N        224-227               CH.sub.3    5-CF.sub.3                                                                           H   H   O      O Cl  OCH.sub.3                                                                               CH                             CH.sub.3    5-CF.sub.3                                                                           H   H   O      O CH.sub.3                                                                           OCH.sub.3                                                                               CH                             CH.sub.3    5-CF.sub.3                                                                           H   H   O      O CH.sub.3                                                                           CH.sub.3 CH                             CH.sub.3    5-CF.sub.3                                                                           H   H   O      O CH.sub.3 O                                                                         CH.sub.3 O                                                                              N                              CH.sub.3    5-CF.sub.3                                                                           H   H   O      O CH.sub.3                                                                           CH.sub.3 N                              CH.sub.3    5-CF.sub.3                                                                           H   H   O      O CH.sub.3                                                                           OCH.sub.3                                                                               N                              CH.sub.3    5-CF.sub.3                                                                           H   H   O      O OCH.sub.3                                                                          N(CH.sub.3).sub.2                                                                       N                              CH.sub.3 CH.sub.2                                                                          5-CF.sub.3                                                                           H   H   O      O Cl  OCH.sub.3                                                                               CH                             CH.sub.3 CH.sub.2                                                                          5-CF.sub.3                                                                           H   H   O      O CH.sub.3 O                                                                         CH.sub.3 O                                                                              CH                             CH.sub.3 CH.sub.2                                                                          5-CF.sub.3                                                                           H   H   O      O CH.sub.3                                                                           CH.sub.3 CH                             CH.sub.3 CH.sub.2                                                                          5-CF.sub.3                                                                           H   H   O      O CH.sub.3                                                                           OCH.sub.3                                                                               CH                             CH.sub.3 CH.sub.2                                                                          5-CF.sub.3                                                                           H   H   O      O CH.sub.3 O                                                                         CH.sub.3 O                                                                              N                              CH.sub.3 CH.sub.2                                                                          5-CF.sub.3                                                                           H   H   O      O CH.sub.3                                                                           CH.sub.3 O                                                                              N                              CH.sub.3 CH.sub.2                                                                          5-CF.sub.3                                                                           H   H   O      O CH.sub.3                                                                           CH.sub.3 N                              CH.sub.3 CH.sub.2                                                                          5-CF.sub.3                                                                           H   H   O      O CH.sub.3 O                                                                         N(CH.sub.3).sub.2                                                                       N                              CH.sub.3    5-CF.sub.3                                                                           H   H                                                                                   ##STR61##                                                                            O Cl  OCH.sub.3                                                                               CH                             CH.sub.3    5-CF.sub.3                                                                           H   H                                                                                   ##STR62##                                                                            O CH.sub.3 O                                                                         CH.sub.3 O                                                                              CH                             CH.sub.3    5-CF.sub.3                                                                           H   H                                                                                   ##STR63##                                                                            O CH.sub.3                                                                           CH.sub.3 CH                             CH.sub.3    5-CF.sub.3                                                                           H   H                                                                                   ##STR64##                                                                            O CH.sub.3                                                                           CH.sub.3 O                                                                              CH                             CH.sub.3    5-CF.sub.3                                                                           H   H                                                                                   ##STR65##                                                                            O CH.sub.3                                                                           CH.sub.3 N                              CH.sub.3    5-CF.sub.3                                                                           H   H                                                                                   ##STR66##                                                                            O CH.sub.3 O                                                                         CH.sub.3 O                                                                              N                              CH.sub.3    5-CF.sub.3                                                                           H   H                                                                                   ##STR67##                                                                            O CH.sub.3                                                                           CH.sub.3 O                                                                              N                              CH.sub.3    5-CF.sub.3                                                                           H   H                                                                                   ##STR68##                                                                            O CH.sub.3 O                                                                         N(CH.sub.3).sub.2                                                                       N                              CH.sub.3    5-Cl  H   H                                                                                   ##STR69##                                                                            O CH.sub.3                                                                           CH.sub.3 CH                             CH.sub.3    5-Cl  H   H                                                                                   ##STR70##                                                                            O CH.sub.3 O                                                                         CH.sub.3 O                                                                              CH                             CH.sub.3    5-Cl  H   H                                                                                   ##STR71##                                                                            O CH.sub.3 O                                                                         CH.sub.3 CH                             CH.sub.3    5-Cl  H   H                                                                                   ##STR72##                                                                            O Cl  CH.sub.3 O                                                                              CH                             CH.sub.3    5-Cl  H   H                                                                                   ##STR73##                                                                            O CH.sub.3                                                                           CH.sub.3 N                              CH.sub.3    5-Cl  H   H                                                                                   ##STR74##                                                                            O CH.sub.3 O                                                                         CH.sub.3 O                                                                              N                              CH.sub.3    5-Cl  H   H                                                                                   ##STR75##                                                                            O CH.sub.3 O                                                                         CH.sub.3 N                              CH.sub.3    5-Cl  H   H                                                                                   ##STR76##                                                                            O CH.sub.3 O                                                                         N(CH.sub.3).sub.2                                                                       N                              __________________________________________________________________________

                                      TABLE II                                     __________________________________________________________________________      ##STR77##                                                                     R.sub.1  R.sub.2                                                                            R.sub.3                                                                           R.sub.4                                                                            Q   W X.sub.1                                                                           Y.sub.1                                                                            n m.p. (°C.)                           __________________________________________________________________________     CH.sub.3 H   H  H   O   O O  H   1                                             CH.sub.3 H   H  H   O   O O  CH.sub.3                                                                           1                                             CH.sub.3 H   H  H   O   O O  OCH.sub.3                                                                          1                                             CH.sub.3 H   H  H   O   O O  H   2                                             CH.sub.3 H   H  H   O   O O  CH.sub.3                                                                           2                                             CH.sub.3 H   H  H   O   O O  OCH.sub.3                                                                          2                                             CH.sub.3 H   H  H                                                                                   ##STR78##                                                                         O O  OCH.sub.3                                                                          2                                             CH.sub.3 5-Cl                                                                               H  H   O   O O  CH.sub.2                                                                           1                                             CH.sub.3 5-Cl                                                                               H  H   O   O O  OCH.sub.3                                                                          1                                             CH.sub.3 5-Cl                                                                               H  H   O   O CH.sub.2                                                                          CH.sub.3                                                                           1                                             CH.sub.3 5-Cl                                                                               H  H   O   O CH.sub.2                                                                          OCH.sub.3                                                                          1                                             CH.sub.3 5-Cl                                                                               H  H   O   O O  CH.sub.3                                                                           2                                             CH.sub.3 5-Cl                                                                               H  H   O   O O  OCH.sub.3                                                                          2                                             (CH.sub.2).sub.3 CH.sub.3                                                               H   H  H   O   O O  OCH.sub.3                                                                          1                                             (CH.sub.2).sub.2 CH.sub.2 Cl                                                            H   H  H   O   O O  OCH.sub.3                                                                          1                                              ##STR79##                                                                              H   H  H   O   O O  OCH.sub.3                                                                          1                                              ##STR80##                                                                              H   H  H   O   O O  OCH.sub.3                                                                          1                                              ##STR81##                                                                              H   H  H   O   O O  OCH.sub.3                                                                          1                                             (CH.sub.2).sub.2 CH.sub.3                                                               H   H  H   O   O O  OCH.sub.3                                                                          1                                             CH.sub.2 CH.sub.2 Cl                                                                    H   H  H   O   O O  OCH.sub.3                                                                          1                                             CH.sub. 2 CH.sub.2 Cl                                                                   H   H  H   O   O O  CH.sub.3                                                                           1                                             CH.sub.2 CH.sub.2 Cl                                                                    H   H  H   O   O O  OCH.sub.3                                                                          2                                             CH.sub.3 5-F H  H   O   O O  OCH.sub.3                                                                          1                                             CH.sub.3 5-Cl                                                                               4-Cl                                                                              H   O   O O  OCH.sub.3                                                                          1                                             CH.sub.3 6-CH.sub.3                                                                         H  H   O   O O  OCH.sub.3                                                                          1                                             CH.sub.3 H   H  H                                                                                   ##STR82##                                                                         O O  OCH.sub.3                                                                          2                                             CH.sub.3 H   H  H                                                                                   ##STR83##                                                                         O O  CH.sub.3                                                                           1                                             CH.sub.3 H   H  H   O   S O  OCH.sub.3                                                                          1                                             CH.sub.3 H   H  H   O   S O  CH.sub.3                                                                           1                                             CH.sub.3 H   H  CH.sub.3                                                                           O   O O  CH.sub.3                                                                           1                                             CH.sub.3 H   H  CH.sub.3                                                                           O   O CH.sub.2                                                                          CH.sub.3                                                                           1                                             CF.sub.3 H   H  H   O   O O  CH.sub.3                                                                           1                                             CH.sub.2 CH.sub.2 OCH.sub.3                                                             H   H  H   O   O O  CH.sub.3                                                                           1                                             CH.sub.3 H   H  OCH.sub.3                                                                          O   O O  CH.sub.3                                                                           1                                             CH.sub.3 H   H  H   O   O CH.sub.2                                                                          OCH.sub.3                                                                          2                                             CH.sub. 3                                                                               H   H  H   O   O O  Cl  1                                             CH.sub.3 H   H  H   O   O O  Cl  2                                             __________________________________________________________________________

                  TABLE III                                                        ______________________________________                                          ##STR84##                                                                                                               m.p.                                 R.sub.1   R.sub.2 R.sub.3 R.sub.4                                                                         QW    X.sub.2 Y.sub.2                                                                         (°C.)                         ______________________________________                                         CH.sub.3  H       H H      OO    OCH.sub.3 OCH.sub.3                           CH.sub.3  H       H H      OO    OCH.sub.3 CH.sub.3                            CH.sub.3  H       H H      OS    OCH.sub.3 OCH.sub.3                           CH.sub.3  H       H CH.sub.3                                                                              OO    OCH.sub.3 OCH.sub.3                           CH.sub.3  H       H H      OO    CH.sub.3 CH.sub.3                             CH.sub.3  H       H CH.sub.3                                                                              OO    CH.sub.3 CH.sub.3                             CH.sub.3  H       H H                                                                                      ##STR85##                                                                           OCH.sub.3 OCH.sub.3                           CF.sub.3  H       H H      OO    OCH.sub.3 OCH.sub.3                           CH.sub.2 CH.sub. 2 OCH.sub.3                                                             H       H H      OO    OCH.sub.3 OCH.sub.3                            ##STR86##                                                                               H       H H      OO    OCH.sub.3 OCH.sub.3                           CH.sub.3  5-Cl    H H      OO    OCH.sub.3 OCH.sub.3                           CH.sub.3  5-CH.sub.3                                                                             H H      OO    OCH.sub.3 OCH.sub.3                           CH.sub.3  H       H OCH.sub.3                                                                             OO    OCH.sub.3 OCH.sub.3                           ______________________________________                                    

                  TABLE IV                                                         ______________________________________                                          ##STR87##                                                                                                               m.p.                                 R.sub.1R.sub.2                                                                              R.sub.3R.sub.4                                                                          QW      X.sub.2                                                                              Y.sub.2                                                                              (°C.)                         ______________________________________                                         CH.sub.3H    HH       OO      OCH.sub.3                                                                            OCH.sub.3                                  CH.sub.3H    HH       OO      OCH.sub.3                                                                            OCH.sub.3                                  CH.sub.3H    HH       OS      OCH.sub.3                                                                            OCH.sub.3                                  CH.sub.3H    HCH.sub.3                                                                               OO      OCH.sub.3                                                                            OCH.sub.3                                  CH.sub.3H    HH       OO      CH.sub.3                                                                             CH.sub.3                                   CH.sub.3H    HCH.sub.3                                                                               OO      CH.sub.3                                                                             CH.sub.3                                   CH.sub.3H    HH                                                                                       ##STR88##                                                                             OCH.sub.3                                                                            OCH.sub.3                                  CF.sub.3H    HH       OO      OCH.sub.3                                                                            OCH.sub.3                                  CH.sub.2 CH.sub.2 OCH.sub.3H                                                                HH       OO      OCH.sub.3                                                                            OCH.sub.3                                   ##STR89##   HH       OO      OCH.sub.3                                                                            OCH.sub.3                                  CH.sub.35-Cl HH       OO      OCH.sub.3                                                                            OCH.sub.3                                  CH.sub.35-CH.sub.3                                                                          HH       OO      OCH.sub.3                                                                            OCH.sub.3                                  CH.sub.3H    HOCH.sub.3                                                                              OO      OCH.sub.3                                                                            OCH.sub.3                                  ______________________________________                                    

                  TABLE V                                                          ______________________________________                                          ##STR90##                                                                     R.sub.1   R.sub.2 R.sub.3   W   IR (cm.sup.-1)                                 ______________________________________                                         CH.sub.3  H       H         O   2210                                            -n-Bu    H       H         O   2220                                           CH.sub.3  5-Cl    H         O   2210                                           C.sub.2 H.sub.5                                                                          H       H         O   2210                                            -n-Pr    H       H         O   2210                                           CH.sub.3  5-CH.sub.3                                                                             H         O   2230                                           CH.sub.3  3-Cl    H         O   2220                                           CF.sub.3  H       H         O   2220                                           ______________________________________                                    

Formulations

Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:

                  TABLE VI                                                         ______________________________________                                                     Active  Weight Percent*                                                        Ingredient                                                                             Diluent(s)                                                                               Surfactant(s)                                    ______________________________________                                         Wettable Powders                                                                             20-90      0-74     1-10                                         Oil Suspensions,                                                                              3-50     40-95     0-15                                         Emulsions, Solutions,                                                          (including Emulsifiable                                                        Concentrates)                                                                  Aqueous Suspension                                                                           10-50     40-84     1-20                                         Dusts          1-25     70-99     0-5                                          Granules and Pellets                                                                         0.1-95      5-99.9  0-15                                         High Strength 90-99      0-10     0-2                                          Compositions                                                                   ______________________________________                                          *Active ingredient plus at least one of a Surfactant or a Diluent equals       100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, N.J., but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0° C. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc.

The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.

For further information regarding the art of formulation, see for example:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;

H. Glysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4;

G. C. Klingman, "Weed Control as a Science", John Wiley & Sons, Inc., New York, 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwise indicated.

EXAMPLE 9 Wettable Powder

    ______________________________________                                         N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-                                                         80%                                                hydroxybenzenesulfonamide, methanesulfonate                                    sodium alkylnaphthalenesulfonate                                                                           2%                                                 sodium ligninsulfonate      2%                                                 synthetic amorphous silica  3%                                                 kaolinite                   13%                                                ______________________________________                                    

The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns and then reblended.

EXAMPLE 10 Wettable Powder

    ______________________________________                                         2-hydroxy-N--[(4-methoxy-6-methylpyrimidin-2-yl)amino-                                                      50%                                               carbonyl]benzenesulfonamide, methanesulfonate                                  sodium alkylnaphthalenesulfonate                                                                            2%                                                low viscosity methyl cellulose                                                                              2%                                                diatomaceous earth           46%                                               ______________________________________                                    

The ingredients are blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in diameter. The product is reblended before packaging.

EXAMPLE 11 Granule

    ______________________________________                                         Wettable Powder of Examp1e 10                                                                          5%                                                     attapulgite granules   95%                                                     (U.S.S. 20-40 mesh; 0.84-0.42 mm)                                              ______________________________________                                    

A slurry of wettable powder containing ≈25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.

EXAMPLE 12 Extruded Pellet

    ______________________________________                                         2-hydroxy-N--[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-                                                      25%                                               aminocarbonyl]benzenesulfonamide, methane-                                     sulfonate                                                                      anhydrous sodium sulfate     10%                                               crude calcium ligninsulfonate                                                                                5%                                               sodium alkylnaphthalenesulfonate                                                                             1%                                               calcium/magnesium bentonite  59%                                               ______________________________________                                    

The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.

EXAMPLE 13 Oil Suspension

    ______________________________________                                         N--[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-                                                         25%                                                 hydroxybenzenesulfonamide, methanesulfonate                                    polyoxyethylene sorbitol hexaoleate                                                                        5%                                                 highly aliphatic hydrocarbon oil                                                                          70%                                                 ______________________________________                                    

The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water.

EXAMPLE 14 Wettable Powder

    ______________________________________                                         N--[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-                                                     20%                                               hydroxybenzenesulfonamide, methanesulfonate                                    sodium alkylnaphthalenesulfonate                                                                            4%                                                sodium ligninsulfonate       4%                                                low viscosity methyl cellulose                                                                              3%                                                attapulgite                  69%                                               ______________________________________                                    

The ingredients are thoroughly blended. After grinding in a hammer-mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.

EXAMPLE 15 Low Strength Granule

    ______________________________________                                         N--[(4,6-dimethoxy-1,3,5-triazin-2-yl)(methyl)amino-                                                       1%                                                 carbonyl]-2-hydroxybenzenesulfonamide,                                         methanesulfonate                                                               N,N--dimethylformamide      9%                                                 attapulgite granules        90%                                                (U.S.S. 20-40 sieve)                                                           ______________________________________                                    

The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged.

EXAMPLE 16 Aqueous Suspension

    ______________________________________                                         N--[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-                                                       40%                                              hydroxybenzenesulfonamide, methanesulfonate                                    polyacrylic acid thickener   0.3%                                              dodecylphenol polyethylene glycol ether                                                                     0.5%                                              disodium phosphate             1%                                              monosodium phosphate         0.5%                                              polyvinyl alcohol            1.0%                                              water                        56.7%                                             ______________________________________                                    

The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size.

EXAMPLE 17 Solution

    ______________________________________                                         N--[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-                                                          5%                                                 hydroxybenzenesulfonamide, methanesulfonate,                                   sodium salt                                                                    water                      95%                                                 ______________________________________                                    

The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use.

EXAMPLE 18 Low Strength Granule

    ______________________________________                                         2-hydroxy-N--[(4-methoxy-6-methylpyrimidin-2-yl)amino-                                                       0.1%                                             carbonyl]benzenesulfonamide, methanesulfonate                                  attapulgite granules         99.9%                                             (U.S.S. 20-40 mesh)                                                            ______________________________________                                    

The active ingredient is dissolvd in a solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After spraying of the solution has been completed, the material is warmed to evaporate the solvent. The material is allowed to cool and then packaged.

EXAMPLE 19 Granule

    ______________________________________                                         N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-                                                        80%                                                 hydroxybenzenesulfonamide, methanesulfonate                                    wetting agent               1%                                                 crude ligninsulfonate salt (containing                                                                    10%                                                 5-20% of the natural sugars)                                                   attapulgite clay            9%                                                 ______________________________________                                    

The ingredients are blended and milled to pass through a 100 mesh screen. This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material. The fluidization and spraying are continued until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, optionally with heat, until the water content is reduced to the desired level, generally less than 1%. The material is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use.

EXAMPLE 20 High Strength Concentrate

    ______________________________________                                         N--[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-                                                      99%                                              hydroxybenzenesulfonamide, methanesulfonate                                    silica aerogel               0.5%                                              synthetic amorphous silica   0.5%                                              ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary.

EXAMPLE 21 Wettable Powder

    ______________________________________                                         2-hydroxy-N--[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-                                                       90%                                              aminocarbonyl]benzenesulfonamide,                                              methanesulfonate                                                               dioctyl sodium sulfosuccinate                                                                               0.1%                                              synthetic fine silica        9.9%                                              ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce particles essentially all below 100 microns. The material is sifted through a U.S.S. No. 50 screen and then packaged.

EXAMPLE 22 Wettable Powder

    ______________________________________                                         N--[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-                                                      40%                                               hydroxybenzenesulfonamide, methanesulfonate                                    sodium ligninsulfonate       20%                                               montmorillonite clay         40%                                               ______________________________________                                    

The ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and then packaged.

EXAMPLE 23 Oil Suspension

    ______________________________________                                         2-hydroxy-N--[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-                                                      35%                                               aminocarbonyl]benzenesulfonamide,                                              1-propanesulfonate            6%                                               blend of polyalcohol carboxylic                                                esters and oil soluble petroleum                                               sulfonates                                                                     xylene                       59%                                               ______________________________________                                    

The ingredients are combined and ground together in a sand mill to produce particles essentially all below 5 microns. The product can be used directly, extended with oils, or emulsified in water.

EXAMPLE 24 Dust

    ______________________________________                                         N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-                                                          10%                                               hydroxybenzenesulfonamide, 1-propanesulfonate                                  attapulgite                  10%                                               Pyrophyllite                 80%                                               ______________________________________                                    

The active ingredient is blended with attapulgite and then passed through a hammer-mill to produce particles substantially all below 200 microns. The ground concentrate is then blended with powdered pyrophyllite until homogeneous.

Utility

The compounds of the present invention are active herbicides. They have utility for broad-spectrum pre- and/or post-emergence weed control in areas where complete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, oil-well sites, drive-in theaters, around billboards, highway and railroad structures. By properly selecting rate, time and method of application, compounds of this invention may also be used to modify plant growth beneficially, and also to selectively control weeds in crops such as wheat, barley, rice, corn and soybeans.

The precise amount of the compounds of Formula I to be used in any given situation will vary according to the particular end result desired, the amount of foliage present, the weeds to be controlled, the crop species involved, the soil type, the formulation and mode of application, weather conditions, etc. Since so many variables play a role, it is not possible to state a rate of application suitable for all situations. Broadly speaking, the compounds of this invention are used at levels of about 0.001 to 20 kg/ha with a preferred range of 0.01 to 10 kg/ha. In general, the higher rates of application from within this range will be selected for adverse conditions or where extended persistence in soil is desired.

The compounds of Formula I may be combined with other herbicides and are particularly useful in combination with the ureas: such as 3-(3,4-dichlorophenyl)-1,1-dimethylurea(diuron); the triazines: such as 2-chloro-4-(ethylamino)-6-(isopropylamino)-s-triazine(atrazine); the uracils: such as 5-bromo-3-sec-butyl-6-methyluracil(bromacil); N-(phosponomethyl)glycine(glyphosate); 3-cyclohexyl-1-methyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione(hexazinone); N,N-dimethyl-2,2-diphenylacetamide(diphenamid); 2,4-dichlorophenoxyacetic acid (2,4-D) (and closely related compounds); 4-chloro-2-butynyl-3-chlorophenylcarbamate(barban); S-(2,3-dichloroallyl)-diisopropylthiocarbamate(diallate); S-(2,3,3-trichloroallyl)-diisopropylthiocarbamate(triallate); 1,2-dimethyl-3,5-diphenyl-1H-pyrazolium methyl sulfate(difenzoquat methyl sulfate); methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate(diclofop methyl); 4-amino-6-tert-butyl-3-(methylthio)-1,2,4-triazin-5(4H)-one(metribuzin); 3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea(linuron); 3-isopropyl-1H-2,1,3-benzothiodiazin-4(3H)-one-2,2-dioxide(bentazon); α,α,α-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine(trifluralin); 1,1'-dimethyl-4,4'-dipyridinium ion(paraquat); monosodium methanearsonate (MSMA); 2-chloro-2',6'-diethyl(methoxymethyl)acetanilide(alachlor); 1,1-dimethyl-3-(α,α,α-trifluoro-m-tolyl)urea(fluometuron); 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid, methyl ester(acifluorfen-methyl); 3-amino- 2,5-dichlorobenzoic acid(chloramben); N-(2-chloroethyl)-2,6-dinitro-N-propyl-4-trifluoromethyl)aniline(fluchloralin); 3,4-dinitro-N,N-dipropylsulfanilamide(oryzalin); N-(1-ethylpropyl)-3,4-dimethyl-2,6-dinitrobenzeneamine(pendimethalin); N-(cyclopropylmethyl)-α,α,α-trifluoro-2,6-dinitro-N-propyl-p-toluidine(profluralin); 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl)acetamide(metolachlor); 4-(6-chloroquinoxalinyl-2-oxy)phenoxypropionate C₁ -C₅ alkyl esters, such as methyl ester, butyl ester, ethyl ester, pentyl ester; ethoxyethoxyethyl 4-(6-chloroquinoxalinyl-2-oxy)phenoxypropionate; butyl 2-[4-[5-(trifluoromethyl)-2-pyridinyloxy]phenoxy]propanoate(fluazifop-butyl); N-[2,4-dimethyl-5-[[(trifluoromethyl)sulfonyl]amino]phenyl]acetamide(mefluidide); 2-[1-(ethoxyimino)butyl]-5-[2-(ethylthio)propyl]-3-hydroxy-2-cyclohexene-1-one(sethoxydim); 2-s-butyl-4,6-dinitrophenol(dinoseb); 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB); propargyl 2-[4-(3,5-dichloropyridin-2-yloxy)phenoxy]propanoate (CGA 82725); methyl 2-[4-(3-chloro-5-trifluoromethylpyridin-2-yloxy)phenoxy]propanoate (DOWCO 453); 5-(2-chloro-4-trifluoromethylphenoxy)-N-methylsulfonyl-2-nitrobenzamide(fomesafen); 2-[1-(2,5-dimethylphenyl)ethylsulfonyl]pyridine-N-oxide (UBI-S-734); and 2-chloro-1-(3-ethoxy-4-nitrophenoxy)-4-(trifluoromethyl)benzene(oxyfluorfen).

The activity of these compounds was discovered in greenhouse tests. The tests are described and data resulting from them are shown below.

Test A

Seeds of crabgrass (Digitaria spp.), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), cassia (Cassia tora), morningglory (Ipomoea sp.), cocklebur (Xanthium spp.), sorghum, corn, soybean, rice, wheat and nutsedge tubers (Cyperus rotundus) were planted in a growth medium and treated pre-emergence with the chemicals dissolved in a non-phytotoxic solvent solution of the compounds of Table A. At the same time, cotton having five leaves (including cotyledonary ones), bush beans with the third trifoliate leaf expanding, crabgrass and barnyardgrass with two leaves, wild oats with two leaves, cassia with three leaves (including cotyledonary ones), morningglory and cocklebur with four leaves (including the cotyledonary ones), sorghum and corn with four leaves, soybean with two cotyledonary leaves, rice with three leaves, wheat with one leaf, and nutsedge with three-five leaves were sprayed with a non-phytotoxic solvent solution of the compounds of Table A. Other containers of the above mentioned weeds and crops were treated pre- or post-emergence with the same non-phytotoxic solvent so as to provide a solvent control. A set of untreated control plants was also included for comparison. Pre-emergence and post-emergence treated plants and controls were maintained in a greenhouse for sixteen days, then all treated plants were compared with their respective controls and rated visually for response to treatment.

The following rating system was used:

0=no effect

10=maximum effect

C=chlorosis or necrosis

D=defoliation

E=emergence inhibition

G=growth retardation

H=formative effects

U=unusual pigmentation

6Y=abscised buds or flowers

P=terminal bud kill

B=burn

X=axillary stimulation ##STR91##

    TABLE A         Cmpd. 1 Cmpd. 2 Cmpd. 3 Cmpd. 4 Cmpd. 5 Cmpd. 6 Cmpd. 7 Cmpd. 8 Cmpd.      9 Cmpd. 10 Cmpd. 11 Cmpd. 12 Cmpd. 13 Cmpd. 14 Cmpd. 15 Cmpd. 16 Rate      kg/ha 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.1      0.1        POST-EMERGENCE Bush bean 9C 9C 9C 9C 9C 9C 1C,2G 10G,9C 9G,3H,6C      7G,3H,7C 2C,2H 1C,2H 6C,9G,6Y 6C,9G,6Y 0 0 Cotton 10C 9C 10C 9C 9C 9C 9C      10G,9C 10G,8C 10G,8C 3C,2H,6G 1C 3C,3H,9G 3C,3H,9G 0 0 Morningglory 10C      10C 10C 10C 10C 10C 9C 10G,9C 7G,9C 10G,5C 9C 1C,5G 4C,9H 3C,9H 0 0      Cocklebur 10C 10C 9C 10C 9C 9C 9C 10G,9C 10C 10G,7C 3C,9G 1C 4C,9H 2C,8G      0 0 Cassia 9C 9C 9C 9C 9C 6C,9G 5C,9G 10C 10G,8C 10G,8C 0 0 3C 1C 0 0      Nutsedge 9C 9C 9C 1C,5G 5G 1C,5G 2C,5G 10G,7C 10G,6C 10G,7C 0 0 0 0 0 0      Crabgrass 9C 9C 9C 4C,9G 2C,9G 9C 3G 0 8G,3C 0 0 0 0 0 0 0 Barnyardgrass      10C 10C 10C 4C,9H 5C,9H 9C 0 10G,6C 10C 10G,9C 2H 0 0 0 0 0 Wild Oats      2C,9G 4C,9G 5C,9G 0 1C,4G 3C,9G 0 0 9G,3C 10G,6C 0 0 0 0 0 0 Wheat 1C,2G      5C,9G 5C,9G 0 0 1C 0 0 3C,2C 3G,2C 0 0 0 0 0 0 Corn 5C,9G 9C 9C 4U,9G      6C,9G 6C,9H 3C,9H 7G,5H 10G,8C 10G,3H 0 0 0 0 0 0 Soybean 9C 9C 9C 9C 9C      9C 9C 10G,7C 10G,8C 7G,7C 2H,6G 1H 2H,6G 2H,5G 0 0 Rice 9C 9C 9C 9C 9C      9C 6G 8G,3C 10C 10C 1C 0 0 0 0 0 Sorghum 9C 10C 9C 2C,9H 2C,9H 6C,9G      1C,3G 10G,4C 10C 10G,9C 0 6H 0 0 0 0 PRE-EMERGENCE Morningglory 9G 9G 9C 9      C 9C 9C 1C,3G 8G,5C 8G,9C 8G,9C 7G 0 3C,9G 4C,9G 0 0 Cocklebur 9H 9H 9H      9H 9H 9H 8H 8G,3H 9G,9P 9G,9P 5H 0 8H,3C 7H,3C 0 0 Cassia 9C 5C,9G 6C,9G      6C,9G 6C,9G 6C,9G 2C,2H 9G,5C 9G,9C 8C,9G 0 0 2C 0 0 0 Nutsedge 10E 10E      10E 1C,7G 1C,6G 6G 0 10E 10E 10E 0 0 0 0 0 0 Crabgrass 9C 6C,9G 2C,8G      2C,5G 2C,6G 1C,6G 0 3G 5G,3H 3G 0 0 0 0 0 0 Barnyardgrass 5C,9H 9C 3C,9H      7C,9H 2C,9H 7C,9H 0 8G,5H 9G,6C 8G,5H 0 0 0 0 0 0 Wild Oats 1U,9G 5C,9H      4C,9H 8G 1C,7G 3C,9G 0 5G,3H 8G,3C 7G,5H 0 0 0 0 0 0 Wheat 5G 5C,9H      1C,9H 3G 0 8G 0 0 7G 7G 0 0 0 0 0 0 Corn 2U,9G 10E 10E 3C,9H 9H 9H 3G 6G      9G 9G,9C 0 0 0 0 0 0 Soybean 9H 9H 9H 9H 9H 9H 1C,2H 8G,5H 9G,5H 8G,5C 0      0 0 0 0 0 Rice 10E 10E 10E 10E 10E 10E 1C 8G,6C 8G,8C 10E 3G 0 0 0 0 0      Sorghum 7C,9H 6C,9H 10H 1C,9G 5C,9H 7C,9H 0 8G,5G 9G,9C 9G,9C 0 0 0 0 0      0   Cmpd. 17 Cmpd. 18 Cmpd. 19 Cmpd. 20 Cmpd. 21 Cmpd. 22 Cmpd. 30 Cmpd.      31 Cmpd. 32 Cmpd. 33 Cmpd. 34 Cmpd. 35 Cmpd. 36 Cmpd. 37 Rate kg/ha 0.05      0.05 0.05 0.05 0.05 0.1 0.05 0.05 0.05 0.05 0.05 0.1 0.05 0.05        POST-EMERGENCE Bush bean 3C,5G,6Y 9C,7G 6C,7G,6Y 2G 9C,6G,6Y 3C,4G,6Y      3C,9G,6Y 9C 9D,9G,6Y 9D,9G,6Y 4C,6G,6Y 2G 5C,9G,6Y 9C Cotton 7C,6G 8C,7G      9C,6G 5C,4G 9C,5G 0 5G,9G 6C,9G 3H,6C,9G 6C,9G 3H,6C,9G 3C,3H,7G 9C 9C      Morningglory 10C 5C,4G 10C 10C 10C 0 9C 10C 10C 3C,9G 9C 6C,9G 9C 9C      Cocklebur 10C 8C,7G 10C 10C 10C 0 9C 10C 9C 6C,9G 6C,9G 4C,9G 10C 10C      Cassia 8C,7G 3C,4G 3C,4G 2C 5C,3G 0 9C 9C 9C 3C,7G 3C,5G 2C 5C,9G      Nutsedge 10C 6C,4G 5C,4G 0 3C,4G 0 9C 1C,9G 4C,9G 2C,7G 1C,3G 1C,2G 9G      1C Crabgrass 2C,3G 0 0 2C,2G 7C,6G 0 6C,9G 6G 2C,5G 1C,3G 1C,3G 0 2C,4G      3C Barnyardgrass 10C 7C,6G 2C,3G 7C,6G 10C 0 10C 9C 10C 10C 3C,7H 0      3C,9H 10C Wild Oats 2C 3C,4G 3G 4C,5G 8C,7G 0 2C,8G 1C,8G 9C 1C,2G 0 0      2G 1C Wheat 0 0 2C,2G 0 2C,3G 0 9C 2C,7G 9C 1C,3G 0 0 0 0 Corn 4C,3U,4G      5C,6G 0 10C 7C,6G 0 10C 7U,9G 1C,9G 3U,9G 1C,5G 0 1C,2G 2C Soybean 6C,7G      10C 7C,6G 4C,5G 5C,6G 0 2C,9G 4C,9G 5C,9G 3C,9G 2C,9G 2C,9G 2C,8G 2C      Rice 2C,3G 3C,4G 3C,5G 3C,4G 2C,3G 0 10C 3C,9G 9C 2C,9G 8G 0 4C,9G 2C      Sorghum 3C,4G 2C,4G 2C,4G 4C,5G 6C,5G 0 10C 2C,9G 9C 3C,9G 1C,6H 1C,3G      9C 3U PRE-EMERGENCE Morningglory 7C,7G 10C 7C,6G 10C 10C 0 9G 9C 9G      1C,9H 2C,9G 0 9G 9G Cocklebur 8C,7G 3C,5G 5C,6G 10C 10C 0 9H 9H 9H 9H 9H      0 9H 9H Cassia 8C,8G 7C,6G 5C,4G 5G,6C 7C,6G 0 2C,9G 2C,9G 2C,9G 9G,3C      6C,9G 0 2C,8G 2C,8H Nutsedge 10E 10E 10E 0 7C,5G 0 10E 10E 10E 1C,9G 3G      0 9G 9G Crabgrass 2C,2G 3G,2C 0 4C,5G 5C,7G 0 2C,8G 2C,9G 1C,3G 1C,3G 0      0 1C 1C,3G Barnyardgrass 7C,8G 7C,7G 7C,5G 7C,7G 8C,8G 0 5C,9H 2C,9H      2C,9H 3C,8H 1C,5H 0 2C,8H 2C,9H Wild Oats 2C 7C,6G 2C,6G 2C,5G 5C,6G 0      8G 2C,9H 1C,9G 1C,5G 0 0 1C,6G 1C,8G Wheat 0 3C,5G 0 0 0 0 9G 9G 3C 0 0      0 0 3G Corn 3C,6G 7C,6G 0 7C,8G 8C,8G 0 1C,9G 2C,9G 2C,9H 1C,9G 1C,8G 0      2C,5G 2C,8H Soybean 7C,8G 7C,8G 7C,6G 6C,7G 7C,6G 0 1C,9G 8H 3C,7H 9H      1C,9H 0 1C,4H 2C,5G Rice 10E 8C,8G 8C,7G 10E 10E 0 10E 2C,9H 10E 9H      2C,5G 0 3C,9H 2C,8H Sorghum 3C,6G 5C,8G 7C,7G 7C,8G 7C,8G 0 1C,9H 4C,9G      3C,9H 2C,9G 2C,7G 0 2C,9H 2C,9H         Cmpd. 38 Cmpd. 39 Cmpd. 40 Cmpd. 23 Cmpd. 24 Cmpd. 25 Cmpd. 26 Cmpd.      27 Cmpd. 28 Cmpd. 29 Cmpd. 41 Cmpd. 42 Compound 43  Compound 44 Rate      kg/ha 0.05 0.05 0.4 0.05 0.05 0.05 0.05 0.05 0.4 0.05 0.4 0.4 2 6 2      6      POST-EMERGENCE Bush bean 4C,9G,6Y 9C 0 3G 1H 0 3C,9G,6Y 1C,2G,6Y      0 0 9C 9C 0 3C 0 0 Cotton 5C,9G 9C 1C 0 0 0 2C 1C 0 0 10C 4C,3H,9G 0 3C      0 2C Morningglory 2C,9G 9C 3G 0 2G 0 2C,6H 1C 3B 1C,2G 6C,9G 6C,9G 0 0 0      1C,3G Cocklebur 9C 10C 3G 2G 1C 0 2C,6G 3C,6H 0 0 10C 9C 0 0 0 0 Cassia      5G  0   0     9C 4C,7H 0 1C 0 0 Nutsedge 8G 2G 3G 0 0 0 0 1C 0 0 2C,8G      2C,5G 0 0 0 0 Crabgrass 2C,5G 1C 5G 0 3G 0 0 1C 0 0 2C,6G 4G 0 0 0 0      Barnyardgrass 3C,7H 2G 0 0 0 0 0 0 0 0 5C,9H 1C,6G 0 1C 0 0 Wild Oats 5G      2G 0 0 0 0 0 0 0 0 1C,8G 0 0 0 0 0 Wheat 0 0 0 0 0 0 0 0 0 0 2G 0 0 0 0      0 Corn 2C,4G 1C 0 0 3G 0 2C,3G 1C 0 0 2U,9H 5U,9G 0 0 0 0 Soybean 1H,6G      1H 0 7G 1H 0 2H 2H 0 0 9C 9C 0 1C 0 3G Rice 7G 0 2G 0 4G 0 0 4G 0 0      6C,9G 6C,9G 0 0 0 0 Sorghum 10C 1C 4G 0 2G 0 0 3G 0 0 6U,9G 2C,9G 0 0 0      2C PRE-EMERGENCE Morningglory 1C,6G 9G 3G 0 0 0 0 0 0 0 9C 9C 0 3C 0 2C      Cocklebur 9H 9H 5H 0 2C 0 0 9H 0 0 9H 9H 0 2C,8H 0 5H Cassia 1C 2C,9H 0      0 0 0 0 0 0 0 4C,9G 3C,7G 0 3G 0 5G Nutsedge 5G 2G 0 0 3G 0 0 0 0 0      1C,9G 8G 0 0 0 0 Crabgrass 1C 1C 2G 0 1C 0 0 0 0 0 5G 1C,4G 0 2G 0 0      Barnyardgrass 3C,5G 1C,4H 0 0 0 0 0 0 0 0 4C,9H 4C,9G 0 5C,8H 0 5C Wild      Oats 1C,6G 0 0 0 0 0 0 0 0 0 4C,8G 2C,8G 0 1C,4G 0 0 Wheat 0 0 0 0 0 0 0      0 0 0 8G 2C,8G 0 0 0 0 Corn 2C,7H 1C,3G 0 0 0 0 0 0 0 0 2U,9G 2C,9G 0      2C,5G 0 1C,2G Soybean 2G 1C 1H 1H 1C,1H 0 0 0 0 0 9H 4C,8H 0 0 0 0 Rice      2C,6G 2C 0 0 2C 0 0 0 0 0 10E 10E 0 1C 0 1C Sorghum 2C,9H 1C,7G 0 0 4H 0      0 0 0 0 5C,9H 5C,9G 0 1C,5G 0 2C         Cmpd. 45 Cmpd. 46 Cmpd. 47 Cmpd. 48 Cmpd. 49 Cmpd. 50 Cmpd. 51 Cmpd.      52 Cmpd. 53 Cmpd. 54 Cmpd. 55 Cmpd. 56 Rate kg/ha 0.05 0.05 0.05 0.05      0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05        POST-EMERGENCE Bush bean 4C,9G,6Y 9C 9C 4C,8G,6Y 9C 9C 0 3C,3H,6Y      4C,9G,6Y 1C 3C,9G,6Y 9C Cotton 6C,9G 6C,9G 8C,9G 3C 6C,9G 6C,9G 0 2C,2H      4C,7H 1C,2G 2C,6G 6C,9G Morningglory 6C,9G 9C 7C,9G 3C,8H 4C,9H 4C,9H 0      3C,7H 3C,8G 2C,7H 3C,9G 6C,9G Cocklebur 5C,9G 9C 9C 1C,4G 4C,9H 4C,9G 0      3C,9G 4C,9G 4G 3C,9H 9C Cassia 3C,6H 5C,9H 5C,9G 1C,3G 5C,7H 4C,6H 0 3C      1C,3G 1C 0 5C,8G Nutsedge 5C,9G 10C 9C 3G 2C,4G 3G,5X 0 8G 1C,8G 0 0 0      Crabgrass 3C,7H 4C,9H 9C 0 9C 3C,9G 0 0 0 0 0 0 Barnyardgrass 5C,9H 9C      6C,9H 2C,8H 9C 5C,8H 0 2C,4H 2H 0 4H 0 Wild Oats 2C,8G 3C,9G 2C,9G 2C,7G      3C,9G 2C,4G 0 0 0 0 0 0 Wheat 1C 1C 1C 0 2U,9G 2C 0 0 0 0 0 0 Corn 3G      3C,9H 5U,9G 3C,9H 9C 7U,9C 0 1C,5H 1C 0 3U,9G 0 Soybean 1C,8H 5C,9G 9C      2C,6G,5X 9C 4C,9G 0 2C,6H 2C,8H 1H 3C,9G 2C,8H Rice 3C,9G 5C,9G 5C,9G      2C,8G,5X 6C,9G 5C,9G 0 4G 4G 0 1C,6G 0 Sorghum 2C,9G 5C,9G 8U,9G 2C,9H      9C 9C 0 2C,4G 1C,3G 0 2C,9H 2G PRE-EMERGENCE Morningglory 3C,9H 2C,9H      2H,9G 1C 4C,9H 2C,9G 0 6H,2C 8G,2C 0 8H,2C 9C Cocklebur 2C,8H 9H 9H 0 --      9H 0 3C,8H -- 0 -- 9H Cassia 5C 3C,9G 5C,9G 1C 3C,3H 2C,3H 0 1C 0 0 0      5C,9G Nutsedge 10E 10E 10E 0 1C 3G 0 1C,8G 9G 0 0 5G Crabgrass 1C,5G      3C,8H 2C,8G 0 1C 1C 0 1C 1C 0 0 0 Barnyardgrass 3C,7H 6C,9H 4C,9H 2C      3C,9H 3C,9H 0 2C,8H 3C 2C 1C 2C Wild Oats 3C,8H 3C,9H 9H 3G 3C,9G 2C,5G      0 0 0 0 0 0 Wheat 0 5G 0 0 1C 2C 0 0 0 0 0 0 Corn 2C,8G 9G 9G 1C,3G      3C,9G 2C,9G 0 3C,7G 1C,4G 1C,5G 3C,7G 0 Soybean 2C,2H 9H 9H 1H 3C,5H      2C,5H 0 1C 1C 1H 1C 0 Rice 4C,8H 5C,9H 10E 1C 9H 9H 0 1C,3G 1C,4G 2G      1C,3G 2G Sorghum 3C,9H 10H 3C,9H 1C 10H 5C,9H 0 2C,6G 1C,4G 0 1C,4G      4G

It is noted that certain compounds such as 15, 16, 22-25, 28 and 29 show little if any activity at the levels tested. It is thought that they would demonstrate herbicidal activity at higher rates.

Test B

Two plastic bulb pans were filled with fertilized and limed Fallsington silt loam soil. One pan was planted with corn, sorghum, Kentucky bluegrass and several grassy weeds. The other pan was planted with cotton, soybeans, purple nutsedge (Cyperus rotundus), and several broadleaf weeds. The following grassy and broadleaf weeds were planted: crabgrass (Digitaria sanguinalis), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), johnsongrass (Sorghum halepense), dallisgrass (Paspalum dilatatum), giant foxtail (Seteria faberii), cheatgrass (Bromus secalinus), mustard (Brassica arvensis), cocklebur (Xanthium pensylvanicum), pigweed (Amaranthus retroflexus), morningglory (Ipomoea hederacea), sicklepod (Cassia obtusifolia), teaweed (Sida spinosa), velvetleaf (Abutilon theophrasti), and jimsonweed (Datura stramonium). A 12.5 cm diameter plastic pot was also filled with prepared soil and planted with rice and wheat. Another 12.5 cm pot was planted with sugarbeets. The above four containers were treated pre-emergence with several test compounds within the scope of the invention.

Twenty-eight days after treatment, the plants were evaluated and visually rated for response to the chemical treatments utilizing the rating system described previously for Test A. The data are summarized in Table B.

                                      TABLE B                                      __________________________________________________________________________     PRE-EMERGENCE ON                                                               FALLSINGT0N SILT LOAM                                                                  Compound 1                                                                             Compound 2                                                                             Compound 36                                                                            Compound 39                                                                            Compound 3                             Rate kg/ha                                                                             0.03                                                                               0.12                                                                               0.03                                                                               0.12                                                                               0.06                                                                               0.25                                                                               0.06                                                                               0.25                                                                               0.007                                                                             0.015                                                                              0.03                                                                               0.12                        __________________________________________________________________________     Crabgrass                                                                              7G,2H                                                                              8G,3H                                                                              7G,3H                                                                              8G,3H                                                                              2G  4G  2G  2G  0  0   5G  6G                          Barnyardgrass                                                                          8G,3H                                                                              9G,9C                                                                              9G,8C                                                                              10C 4G  6G,5H                                                                              4G  5G  2G 2G  8G,3H                                                                              9G,9C                       Sorghum 9G,9C                                                                              10C 10C 10E 6G,3H                                                                              8G,5H                                                                              4G  4G,2H                                                                              2G 4G  10C 10E                         Wild Oats                                                                              6G  10C 8G,5C                                                                              9G,9C                                                                              4G  4G  3G  3G  0  0   10C 10C                         Johnsongrass                                                                           8G,7C                                                                              10C 9G,9C                                                                              10C 4G,3H                                                                              6G,3H                                                                              4G  3G  0  3G  10C 10C                         Dallisgrass                                                                            7G  9G,9C                                                                              8G,3H                                                                              8G,3H                                                                              4G  5G  3G  0   0  3G  6G  8G,3H                       Giant foxtail                                                                          6G,3C                                                                              8G,5C                                                                              5G,3C                                                                              10C 4G  6G,3H                                                                              0   2G  0  3G  3C  7G,3C                       Ky. bluegrass                                                                          8G,9C                                                                              10C 8G,9C                                                                              10C 6G  7G  2G  4G  0  2G  10C 8G,8C                       Cheatgrass                                                                             8G,9C                                                                              9G,9C                                                                              10E 10E 6G  7G  0   3G  0  --  10E 10E                         Sugarbeets                                                                             10C 10C 10C 10C 6G,6C                                                                              8G,9C                                                                              9G,8C                                                                              10C -- 4G  10C 10C                         Corn    5G,3U                                                                              8G,5H                                                                              7G,5H                                                                              10C 3G  4G  2G  4G  0  0   10C 10C                         Mustard 10C 10C 10C 10C 10E 10E 8G,8C                                                                              8G,9C                                                                              5G 7G,3C                                                                              10C 10C                         Cocklebur                                                                              6G  --  5G  10C --  8G,7C                                                                              8G,5H                                                                              10C 0  0   7G  8G,5H                       Pigweed 10C 10E 7G  10E 5G,5C                                                                              9G,9C                                                                              4G  6G,4C                                                                              0  10E 9G,9C                                                                              10C                         Nutsedge                                                                               10E 10E 6G  10E 7G  10E 4G  6G  0  0   10E 10E                         Cotton  8G  9G,5C                                                                              6G,3H                                                                              9G,8C                                                                              4G  8G,3H                                                                              8G,3H                                                                              9G,5C                                                                              0  0   8G,3C                                                                              9G,7C                       Morningglory                                                                           5G  9G,9C                                                                              7G  9G,5C                                                                              4G  8G,9C                                                                              9G  9G,3C                                                                              3G 3G  8G  9G,7C                       Cassia  8G,8C                                                                              10C 7G,4C                                                                              9G,9C                                                                              6G  8G,8C                                                                              5G,3C                                                                              7G,8C                                                                              0  0   9G,8C                                                                              9G,8C                       Teaweed 6G  9G,8C                                                                              6G,3H                                                                              8G,6C                                                                              5G,3C                                                                              6G,3C                                                                              6G,2C                                                                              6G,3C                                                                              -- 0   4G  10C                         Velvetleaf                                                                             9G,8C                                                                              10C 8G,8C                                                                              9G,9C                                                                              5G,3H                                                                              8G,8C                                                                              7G,3H                                                                              8G,9C                                                                              0  0   8G,5E                                                                              9G,8C                       Jimsonweed                                                                             7G,3C                                                                              9G,8C                                                                              9G,9C                                                                              9G,9C                                                                              3G  5G,5C                                                                              7G,3C                                                                              8G,5C                                                                              0  0   8G,8C                                                                              9G,9C                       Soybean 8G,5H                                                                              9G,8C                                                                              7G,5H                                                                              9G,8C                                                                              2G  5G,3H                                                                              3G  4G  0  0   8G,5H                                                                              9G,8C                       Rice    8G,3H                                                                              10E 8G,7C                                                                              10E 3G  5G  0   0   3G 6G,3H                                                                              10E 10E                         Wheat   0   3G  5G  8G,9C                                                                              0   0   0   0   0  0   5G  7G,3C                       __________________________________________________________________________

Test C

The high herbicidal activity of two of the compounds from within the scope of the invention is evident from the results obtained in this test. The experiment concerned pre-emergence applications on soil. The containers used were 25 cm diameter plastic pots filled with Fallsington silt loam. One set of pots was planted to weeds, the seeds of which were uniformly mixed with the top 1.2 cm layer of soil. The species selected were: johnsongrass (Sorghum halepense), barnyardgrass (Echinochloa crusgalli), crabgrass (Digitaria sanguinalis), giant foxtail (Setaria faberii), velvetleaf (Abutilon theophrasti), jimsonweed (Datura stramonium), mustard (Brassica arvensis), and pigweed (Amaranthus retroflexus). Another set of pots was planted to the following crops with from one to four species per pot: corn (planting depth 3.7 cm), cotton, soybeans, sunflower, Clinton oats, wheat, Black Valentine beans, rice, sorghum, peas, flax, and peanuts (all at 2.5 cm depth), cucumbers, cabbage, alfalfa, safflower, sugarbeets, tomato, spinach, barley, and Kentucky bluegrass (all at 1.2 cm depth). Immediately after planting, the test chemical was applied to the soil surfaces dissolved in a non-phytotoxic solvent. One pot from the weed phase and one of each of the crop species were left untreated for the purpose of comparison. The treated and untreated pots were promptly watered with approximately 4 mm of simulated rainfall and then held in a greenhouse for several weeks. Visual weed and crop response ratings were made 28 days after treatment utilizing the rating system as described above for Test A. The data are given in Table C.

                                      TABLE C                                      __________________________________________________________________________     PRE-EMERGENCE ON                                                               FALLSINGTON SILT LOAM SOIL                                                            Compound 1      Compound 2                                              Rate kg/ha                                                                            0.0035                                                                             0.0075                                                                             0.0150                                                                             0.03                                                                               0.0075                                                                             0.015                                                                              0.030                                                                              0.06                                        __________________________________________________________________________     Corn               5G,3C           9G,9C                                       Cotton             7G,3H           10E                                         Soybean            4G,2H           9G,5H                                       Peanut             6G              8G,3H                                       Sunflower          5G              9G,5H                                       Oats               4G              6G,2C                                       Wheat              2G              5G                                          Sorghum            7G,5H           10E                                         Sugarbeet          9G,9C           10E                                         Pea                10E             10E                                         Flax               6G              10E                                         Alfalfa            8G,6C           8G,6C                                       Bean               0               8G,5H                                       Spinach            8G,5H           9G,9C                                       Cabbage            8G,6C           8G,7C                                       Tomato             4G              5C,8G                                       Rice               6G              10E                                         Safflower          7G,4C           8G,7C                                       Cucumber           5G              9G,5H                                       Ky. bluegrass      7G              6G,5H                                       Barley             3G              8G,7C                                       Broadleaves                                                                           3G  4G  6G,2H                                                                              --  5G,3C                                                                              7G,5C                                                                              9G,8C                                                                              --                                          Grasses                                                                               0   0   2G  --  6G,3C                                                                              8G,4C                                                                              9G,6C                                                                              --                                          __________________________________________________________________________

Test D

Two ten-inch in diameter plastic pans lined with polyethylene liners were filled with prepared Fallsington silt loam soil. One pan was planted with seeds of wheat (Triticum aestivum), barley (Hordeum vulgare), wild oats (Avena fatua), downy brome (Bromus tectorum), cheatgrass (Bromus secalinus), blackgrass (Alopecurus myosuroides), annual bluegrass (Poa annua), green foxtail (Setaria viridis), quackgrass (Agropyron repens), Italian ryegrass (Lolium multiflorum) and ripgut brome (Bromus rigidus). The other pan was planted with seeds of Russian thistle (Salsola kali), tansy mustard (Descuraina pinnata), smartweed (Polygonum pensylvanicum), tumble mustard (Sisymbrium altissium) kochia (Kochia scoparia), spepherd's purse (Capsella bursa-pastoris), Matricaria inodora, black nightshade (Solanum nigrum), yellow rocket (Barbarea vulgaris), wild mustard (Brassica kaber) and wild buckwheat (Polygonum convolvulus). The above two pans were treated pre-emergence. At the same time two pans in which the above plant species were growing were treated post-emergence. Plant height at the time of treatment ranged from 1-15 cm depending on plant species.

The compounds applied were diluted with a non-phytotoxic solvent and sprayed over-the-top of the pans. An untreated control and a solvent alone control were included for comparison. All treatments were maintained in the greenhouse for 20 days at which time the treatments were compared to the controls and the effects visually rated. The recorded data, presented in Table D, indicate that certain compounds from within the scope of the invention have utility for pre- and/or post-emergence weed control in cereal crops such as wheat and barley.

                                      TABLE D                                      __________________________________________________________________________     Compound 1                                                                               Pre-Emergence    Post-Emergence    Pre-Emergence                                                                           Post-Emergence           Rate kg/ha                                                                               0.002                                                                              0.008                                                                              0.008                                                                               0.015                                                                              0.002                                                                              0.008                                                                               0.008                                                                              0.015                                                                               0.03                                                                               0.06 0.03                                                                               0.06                 __________________________________________________________________________     wheat     0   0   0    0   0   0    0   0    0   2C,3G                                                                               0   1C,2G                barley    0   0   0    1C,6G                                                                              0   0    0   3C,5G                                                                               1C,1G                                                                              6C,8G                                                                               2C,2G                                                                              7C,6G                wild oats 0   0   0    3C,7G                                                                              0   1C   0   3C,2G                                                                               0   8C,8G                                                                               2G  3C,3G                downy brome                                                                              3G  2C,5G                                                                              1G   5C,7G                                                                              3G  5C,7G                                                                               4C,5G                                                                              3G   2C,7G                                                                              10C  7C,7G                                                                              3C,4G                cheatgrass                                                                               5G  4C,7G                                                                              3G   10C 4C,7G                                                                              8C,7G                                                                               8C,7G                                                                              10C  5C,8G                                                                              10C  10C 10C                  blackgrass                                                                               3G  5C,6G                                                                              2G   10C 6G  4C,5G                                                                               7C,7G                                                                              10C  3C,7G                                                                              10C  10C 10C                  annual bluegrass                                                                         5G  2C,6G                                                                              1C,2G                                                                               7C,8G                                                                              3G  3C,6G                                                                               3C,5G                                                                              5C,4G                                                                               5C,7G                                                                              10C  6C,7G                                                                              10C                  green foxtail                                                                            0   2G  3C,4G                                                                               3C,5G                                                                              4G  7C,7G                                                                               7C,7G                                                                              3C,4G                                                                               7C,7G                                                                              9C,8G                                                                               7C,8G                                                                              7C,6G                quackgrass                                                                               3G  3C,5G                                                                              0    8G  3G  6G   2C,3G                                                                              6C,5G                                                                               2C,3G                                                                              10C  3C,6G                                                                              7C,6G                Italian ryegrass                                                                         0   3C,5G                                                                              0    4G  2G  2G   0   3G   1C,3G                                                                              4C,7G                                                                               2C,4G                                                                              4C,5G                ripgut brome                                                                             2G  2C,4G                                                                              0    2C,5G                                                                              2G  5G   0   2G   0   5C,7G                                                                               2C,3G                                                                              3C,5G                Russian thistle                                                                          0   0   1G   8C,7G                                                                              2C,3G                                                                              10C  9C,7G                                                                              10C  2C,3G                                                                              8C,8G                                                                               10C 10C                  tansy mustard                                                                            6G  8C,8G                                                                              8C,8G                                                                               10C 10C 10C  10C 10C  10C 10C  10C 10C                  smartweed --  --  --   --  --  --   --  --   --  --   --  --                   tumble mustard                                                                           3C,8G                                                                              10C 7C,7G                                                                               10C 4C,6G                                                                              10C  10C 10C  10C 10C  10C 10C                  kochia    1G  5G  3G   9C,8G                                                                              3G  4G   10C 8C,7G                                                                               7C,8G                                                                              10C  10C 10C                  shepherd's purse                                                                         3C,5G                                                                              8C,8G                                                                              9C,8G                                                                               10C 10C 10C  10C 10C  10C 10C  10C 10C                  Matricaria inodora                                                                       4G  7C,8G                                                                              7C,7G                                                                               10C 7C,7G                                                                              10C  9C,7G                                                                              10C  7C,8G                                                                              10C  9C,8G                                                                              10C                  black nightshade                                                                         2C,4G                                                                              4C,6G                                                                              6C,7G                                                                               8G  4G  4C,6G                                                                               1C,1G                                                                              0    7C,7G                                                                              3C,8G                                                                               3C,7G                                                                              4C,5G                yellow rocket                                                                            2C,7G                                                                              4C,8G                                                                              7C,7G                                                                               10C 3G  10C  10C 10C  8C,9G                                                                              10C  10C 10C                  wild mustard                                                                             5C,6G                                                                              8C,8G                                                                              7C,7G                                                                               10C 10C 10C  10C 10C  8C,8G                                                                              10C  10C 10C                  wild buckwheat                                                                           3G  2C,4G                                                                              1C,2G                                                                               3C,6G                                                                              2C,4G                                                                              5C,5G                                                                               6C,5G                                                                              10C  3C,4G                                                                              4C,8G                                                                               7C,6G                                                                              10C                  __________________________________________________________________________     Compound 2                                                                               Pre-Emergence    Post-Emergence    Pre-Emergence                                                                           Post-Emergence           Rate kg/ha                                                                               0.002                                                                              0.008                                                                              0.008                                                                               0.015                                                                              0.002                                                                              0.008                                                                               0.008                                                                              0.015                                                                               0.03 0.06                                                                               0.03                                                                               0.06                 __________________________________________________________________________     wheat     0   0   0    2C,2G                                                                              0   1G   1G  5C,5G                                                                               2C,4G                                                                               4C,6G                                                                              1C,2G                                                                              7C,7G                barley    0   3G  3C,4G                                                                               5C,7G                                                                              0   3G   2C,3G                                                                              7C,6G                                                                               6C,7G                                                                               8C,8G                                                                              4C,6G                                                                              10C                  wild oats 0   2C,5G                                                                              2G   8C,8G                                                                              0   2C,5G                                                                               5G  7C,7G                                                                               7C,6G                                                                               9C,8G                                                                              5C,6G                                                                              8C,7G                downy brome                                                                              6G  7C,7G                                                                              3C,7G                                                                               10C 3C,5G                                                                              7C,7G                                                                               7C,7G                                                                              7C,7G                                                                               7C,8G                                                                               10C 8C,7G                                                                              10C                  cheatgrass                                                                               5C,7G                                                                              10C 5C,8G                                                                               10C 6C,7G                                                                              10C  10C 10C  10C  10C 10C 10C                  blackgrass                                                                               3C,6G                                                                              7C,7G                                                                              3C,7G                                                                               10C 2C,6G                                                                              7C,7G                                                                               7C,7G                                                                              10C  8C,7G                                                                               10C 10C 10C                  annual bluegrass                                                                         1C,6G                                                                              7C,7G                                                                              2C,5G                                                                               10C 5C,6G                                                                              10C  6C,5G                                                                              10C  5C,6G                                                                               10C 10C 10C                  green foxtail                                                                            0   4C,5G                                                                              2C,4G                                                                               6C,7G                                                                              3C,5G                                                                              4C,5G                                                                               7C,8G                                                                              6C,6G                                                                               4C,6G                                                                               9C,9G                                                                              8C,8G                                                                              7C,7G                quackgrass                                                                               4G  3C,6G                                                                              4G   8C,9G                                                                              1C,6G                                                                              4C,6G                                                                               6G  7C,6G                                                                               7C,7G                                                                               9C,9G                                                                              4C,6G                                                                              10C                  Italian ryegrass                                                                         3G  5C,7G                                                                              5C,7G                                                                               9C,9G                                                                              1C,5G                                                                              3C,6G                                                                               3C,6G                                                                              10C  7C,8G                                                                               10C 5C,7G                                                                              10C                  ripgut brome                                                                             5G  6G  3C,4G                                                                               9C,9G                                                                              4G  1C,7G                                                                               3G  4C,6G                                                                               6C,7G                                                                               9C,9G                                                                              4C,4G                                                                              9C,8G                Russian thistle                                                                          0   1C,1G                                                                              3C,4G                                                                               9C,9G                                                                              5C,4G                                                                              8C,7G                                                                               10C 10C  5C,6G                                                                               10C 10C 10C                  tansy mustard                                                                            3C,8G                                                                              8C,9G                                                                              7C,8G                                                                               10C 10C 10C  10C 10C  9C,9G                                                                               10C 10C 10C                  smartweed --  --  --   --  --  --   --  --   --   --  --  --                   tumble mustard                                                                           7C,8G                                                                              10C 10C  10C 7C,8G                                                                              8C,8G                                                                               10C 10C  10C  10C 10C 10C                  kochia    2G  5G  7C,8G                                                                               8C,9G                                                                              5G  10C  10C 7C,6G                                                                               9C,8G                                                                               9C,9G                                                                              10C 10C                  shepherd's purse                                                                         8C,8G                                                                              8C,8G                                                                              10C  10C 10C 10C  10C 10C  10C  10C 10C 10C                  Matricaria inodora                                                                       5C,8G                                                                              7C,8G                                                                              7C,7G                                                                               10C 10C 10C  7C,7G                                                                              10C  7C,8G                                                                               10C 8C,7G                                                                              10C                  black nightshade                                                                         3C,4G                                                                              3C,4G                                                                              5C,6G                                                                               2C,7G                                                                              2G  3C,5G                                                                               1C,1G                                                                              0    7C,6G                                                                               5C,8G                                                                              3C,4G                                                                              2G                   yellow rocket                                                                            8G  2C,9G                                                                              7C,7G                                                                               10C 10C 10C  8C,8G                                                                              10C  10C  10C 10C 10C                  wild mustard                                                                             7C,8G                                                                              8C,8G                                                                              7C,8G                                                                               10C 10C 10C  10C 10C  9C,8G                                                                               10C 10C 10C                  wild buckwheat                                                                           2C,1G                                                                              3C,4G                                                                              3C,2G                                                                               3C,4G                                                                              2C,2G                                                                              3C,5G                                                                               6C,6G                                                                              10C  4C,5G                                                                               5C,6G                                                                              7C,8G                                                                              10C                  __________________________________________________________________________                                  Compound 3       Compound 36                                                   Pre-Emergence                                                                          Post-Emergence                                                                          Pre-Emergence                                                                          Post-Emergence                              Rate kg/ha                                                                               0.008                                                                              0.03                                                                               0.008                                                                              0.03 0.015                                                                              0.06                                                                               0.015                                                                              0.06                 __________________________________________________________________________                        wheat     0   1C,2G                                                                              0   1C,2G                                                                               0   0   0   0                                       barley    2G  7C,6G                                                                              0   4C,6G                                                                               0   0   0   0                                       wild oats 1G  7C,7G                                                                              0   7C,5G                                                                               0   0   0   0                                       downy brome                                                                              4G  10C 6C,7G                                                                              7C,7G                                                                               3G  6G  0   3G                                      cheatgrass                                                                               2C,5G                                                                              10C 7C,7G                                                                              10C  7G  10C 1G  3C,5G                                   blackgrass                                                                               7C,7G                                                                              10C 4C,5G                                                                              10C  6G  3C,7G                                                                              2G  5C,4G                                   annual bluegrass                                                                         3C,4G                                                                              5C,6G                                                                              4C,6G                                                                              5C,7G                                                                               6G  7C,7G                                                                              2G  3G                                      green foxtail                                                                            2C,3G                                                                              5C,4G                                                                              2C,4G                                                                              6C,7G                                                                               2G  3C,5G                                                                              1G  2G                                      quackgrass                                                                               0   3C,4G                                                                              2C,3G                                                                              4C,6G                                                                               0   2G  0   0                                       Italian ryegrass                                                                         3G  7C,7G                                                                              3C,6G                                                                              5C,6G                                                                               1G  3G  0   0                                       ripgut brome                                                                             0   10C 1C,2G                                                                              3C,4G                                                                               2G  2C,7G                                                                              0   2G                                      Russian thistle                                                                          0   7C,7G                                                                              3C,2G                                                                              10C  0   1G  0   2G                                      tansy mustard                                                                            4C,5G                                                                              9C,9G                                                                              8C,7G                                                                              10C  2G  2C,5G                                                                              5C,4G                                                                              7C,8G                                   smartweed --  --  --  --   --  --  --  --                                      tumble mustard                                                                           7G  10C 10C 10C  5G  3C,7G                                                                              10C 10C                                     kochia    6G  10C 4G  10C  0   5C,6G                                                                              0   0                                       shepherd's purse                                                                         7C,7G                                                                              10C 9C,8G                                                                              10C  7G  3C,8G                                                                              7C,8G                                                                              10C                                     Matricaria inodora                                                                       6C,7G                                                                              7C,7G                                                                              6C,5G                                                                              9C,8G                                                                               3C,8G                                                                              7C,8G                                                                              7C,7G                                                                              9C,8G                                   black nightshade                                                                         3C,4G                                                                              5C,6G                                                                              4G  8C,8G                                                                               4G  1C,5G                                                                              2G  4C,5G                                   yellow rocket                                                                            7G  7C,7G                                                                              2C,5G                                                                              10C  3C,8G                                                                              10C 7C,7G                                                                              10C                                     wild mustard                                                                             5C,7G                                                                              7C,8G                                                                              10C 10C  7C,8G                                                                              10C 10C 10C                                     wild buckwheat                                                                           0   2C,3G                                                                              2C,2G                                                                              5C,6G                                                                               3G  1C,4G                                                                              1C,2G                                                                              5C,4G                __________________________________________________________________________

Test E

Test samples were formulated and applied directly to the paddy water three days after transplanting of rice. The test was maintained in a greenhouse, and plant response ratings were taken at the stated intervals after application. The data indicate:

    ______________________________________                                         Compound 1                                                                                                Barnyard-                                                                              Water                                       Rate    Rice    Rice       grass*  Chestnut**                                  g/ha    4 Days  4 Weeks    4 Weeks 4 Weeks                                     ______________________________________                                         1       0       0          0       7G                                          4       0       0          0       8G                                          8       0       0          0       9G                                          ______________________________________                                         Compound 36                                                                                           Barnyard-                                                                              Water   Arrow-                                  Rate,                                                                               Rice     Rice     grass*  Chestnut**                                                                             head***                                 g/ha 1 Week   8 Weeks  8 Weeks 8 Weeks 8 Weeks                                 ______________________________________                                          25  0        0        0       10C     0                                       100  0        0        0       10C     0                                       ______________________________________                                          *Echinochloa spp.                                                              **Eleocharis spp.                                                              ***Sagittaria spp.                                                       

It may be seen that compounds from within the scope of the invention can be used for selective weed control in rice.

Test F

The test chemicals, dissolved in a non-phytotoxic solvent, were applied in an overall spray to the foliage and surrounding soil of selected plant species. One day after treatment, plants were observed for rapid burn injury. Approximately fourteen days after treatment, all species were visually compared to untreated controls and rated for response to treatment. The rating system was as described previously for Test A. The data are presented in Table F.

All plant species were seeded in Woodstown sandy loam soil and grown in a greenhouse. The following species were grown in soil contained in plastic pots (25 cm diameter by 13 cm deep): soybeans, cotton, alfalfa, corn, rice, wheat, sorghum, velvetleaf (Abutilon theophrasti), sesbania (Sesbania exaltata), Cassia (Cassia tora), morningglory (Ipomoea hederacea), jimsonweed (Datura stramonium), cocklebur (Xanthium pensylvanicum), crabgrass (Digitaria spp.), nutsedge (Cyperus rotundus), barnyardgrass (Echinochloa crusgalli), giant foxtail (Setaria faberii) and wild oats (Avena fatua). The following species were grown in soil in a paper cup (12 cm diameter by 13 cm deep): sunflower, sugarbeets, and mustard. All plants were sprayed approximately 14 days after planting.

Some of the compounds tested by this procedure are useful for the post-emergence control of weeds in wheat. Compound 39 has utility for the post-emergence control of weeds in soybeans and corn.

                                      TABLE F                                      __________________________________________________________________________     Over-the-Top Soil/Foliage Treatment                                            __________________________________________________________________________             Compound 1          Compound 2                                                                               Compound 3                               Rate kg/ha                                                                             0.06 0.015                                                                               0.007                                                                               0.003                                                                               0.06 0.015                                                                               0.06 0.015                                                                               0.007                                                                               0.003                     __________________________________________________________________________     Soybeans                                                                               10G,7C                                                                              10G,7C                                                                              9G,5C                                                                               9G,5C                                                                               9C   10G,8C                                                                              10G,6C                                                                              10G,4C                                                                              9G,7C                                                                               10G,5C                    Velvetleaf                                                                             10G,7C                                                                              8G,3C                                                                               9G,9C                                                                               10G,9C                                                                              10G,4C                                                                              5G   7G,2C                                                                               5G   8G,8C                                                                               7G                        Sesbania                                                                               9C   9C   10C  10C  10C  9C   9C   9C   8G,5C                                                                               9G,8C                     Cassia  10G,7C                                                                              8G,2C                                                                               9G,5C                                                                               10G,5C                                                                              10G,7C                                                                              7G,3C                                                                               10G,7C                                                                              5G,3C                                                                               10G,5C                                                                              8G,4C                     Cotton  10G,7C                                                                              7G,3C                                                                               10G,9C                                                                              10C  10G,6C                                                                              7G,3C                                                                               10G,6C                                                                              10G,6C                                                                              10C  8G,2C                     Morningglory                                                                           10G,5C                                                                              9G,4C                                                                               10G,8C                                                                              10G,8C                                                                              10C  8G,2C                                                                               9G,4C                                                                               9G,3C                                                                               10G,8C                                                                              7G,1H                     Alfalfa 9C   5C   6G,2C                                                                               6G,2C                                                                               10C  7C   9C   8C   7G   6G,2C                     Jimsonweed                                                                             9C   7G,3C                                                                               0    0    10C  --   9G,3C                                                                               --   --   0                         Cocklebur                                                                              10G,7C                                                                              9G,3C                                                                               7G   5G   10G,8C                                                                              10G,7C                                                                              10G,7C                                                                              10G,7C                                                                              4G,5C                                                                               3G                        Corn    10C  9G,7C                                                                               8G,2H                                                                               9G,1H                                                                               10C  10G,7U                                                                              10C  9G,6C                                                                               9G   9G,1H                     Crabgrass                                                                              8G,4C                                                                               2C   5G   0    10C  6G,1C                                                                               7G,4C                                                                               0    5G,1C                                                                               0                         Rice    8G,3C                                                                               3G,1C                                                                               8G,5C                                                                               7G,2C                                                                               10C  6G,3C                                                                               8G,5C                                                                               7G,3C                                                                               9G,7C                                                                               9G,7C                     Nutsedge                                                                               10C  10C  5G   3G   10C  2C   9G,4C                                                                               9G,3C                                                                               7G   5G                        Barnyardgrass                                                                          10C  10C  9G,4C                                                                               9G,2C                                                                               10C  6G,3C                                                                               10C  9C   9G,4C                                                                               9G,2C                     Wheat   0    0    0    1G   9C   1C   8C   1C   6G   3G                        Giant foxtail                                                                          10G,3C                                                                              7G,3C                                                                               5G   5G   10C  --   --   --   0    0                         Wild Oats                                                                              6G   3G   3G   3G   10C  5C,3C                                                                               10C  7G,3C                                                                               5G   4G                        Sorghum 10C  9C   8G,3C                                                                               7G,4U                                                                               10C  8G,5C                                                                               10C  9C   7G,3U                                                                               9G,6U                     Mustard --   --   10C  10C  --   --   --   --   10C  9G,9C                     Sunflower                                                                              --   --   10C  10C  --   --   --   --   10C  10G,9C                    Sugarbeets                                                                             --   --   10C  9G,9C                                                                               --   --   --   --   10C  9G,9C                     __________________________________________________________________________             Compound 39                         Compound 36                        Rate kg/ha                                                                             0.12 0.06                                                                               0.03 0.015                                                                               0.015 0.015                                                                               0.007 0.12 0.06                                                                               0.015                     __________________________________________________________________________     Soybeans                                                                               10G,7C                                                                              9G,9C                                                                              4G   0    0     3G   0     10C  9G,9C                                                                              9G,7C                     Velvetleaf                                                                             9G,7C                                                                               8G,5C                                                                              10G,5C                                                                              8G,4C                                                                               8G,3C 8G,3C                                                                               7G,3C 10C  10C 8G,7C                     Sesbania                                                                               10C  9G,4C                                                                              10G,7C                                                                              8G,6C                                                                               9G,4C 5G,4C                                                                               7G,4C 10C  10C 10C                       Cassia  9G,7C                                                                               5G,5C                                                                              8G,5C                                                                               5G,5C                                                                               8G,4C 4G,6C                                                                               5G,3C 10C  9G,3C                                                                              8G,3C                     Cotton  9G,7C                                                                               9G,6C                                                                              9G,5C                                                                               8G,4C                                                                               8G,4C 8G,4C                                                                               6G,3C 9G,9C                                                                               8G,8C                                                                              4G,4C                     Morningglory                                                                           9G,8C                                                                               9G,5C                                                                              9G,4C                                                                               9G,5C                                                                               9G,4C 10G,3C                                                                              9G,6C 10C  10C 8G,4C                     Alfalfa 9G,8C                                                                               10C 9G,5C                                                                               5G,2C                                                                               9G,5C 7G   7G,3C 9G   5G,3C                                                                              7G                        Jimsonweed                                                                             0    --  --   --   8G    2C   --    0    0   0                         Cocklebur                                                                              10G,7C                                                                              10G,5C                                                                             10G,5C                                                                              9G,5C                                                                               10G,5C                                                                               10G,4C                                                                              9G,4C 10C  10C 10C                       Corn    0    0   3G,2C                                                                               0    1G,2C 0    2G    2G,1C                                                                               1G,2C                                                                              1G,1C                     Crabgrass                                                                              0    0   0    0    0     0    0     5G   0   0                         Rice    0    0   4G   1G   3G    0    2G    5G   4G  2G                        Nutsedge                                                                               1G   0   3G   0    0     0    5G    7G,5C                                                                               7G,5C                                                                              0                         Barnyardgrass                                                                          0    0   3G   0    0     0    2G    9G,5C                                                                               8G,5C                                                                              6G,2C                     Wheat   0    0   0    0    0     0    0     2G   0   0                         Giant foxtail                                                                          0    0   2G   0    2G    0    1G    3G,2C                                                                               2C  0                         Wild Oats                                                                              0    0   2G   0    1G    2G   0     3G   0   0                         Sorghum 0    0   5G   0    4G    5G   3G    7G,3C                                                                               5G,2C                                                                              2G,2C                     Mustard 10C  10C 10G,5C                                                                              10G,5C                                                                              10G,5C                                                                               9G   10G,5C                                                                               10C  10C 10C                       Sunflower                                                                              10C  10C 10G,8C                                                                              10G,8C                                                                              10G,8C                                                                               10C  10G,8C                                                                               10C  10C 10C                       Sugarbeets                                                                             10G,5C                                                                              10C 9G,3C                                                                               10G,5C                                                                              9G,3C 9G   10G,4C                                                                               9G,3C                                                                               9G,5C                                                                              8G                        __________________________________________________________________________

Test G

This test demonstrates the broadleaf herbicidal properties of compound 39. Approximately 12 soybean plants were grown in a 25 cm. diameter plastic pot. In another pot of equal size the following broadleaf plant species were grown: sugarbeets, velvetleaf, Sesbania, Cassia, mustard, morningglory, alfalfa, jimsonweed, and cocklebur. The plant foliage and surrounding soil were treated with the test chemical dissolved in a non-phytotoxic solvent as an overall spray at the rate of 0.015 kg/ha, when the plants were 17 days old. Visual ratings of herbicidal effects were made 22 days after treatment utilizing the rating system described for Test A.

                  TABLE G                                                          ______________________________________                                         Rate                  0.015                                                    ______________________________________                                         Soybeans              0                                                        Sugarbeets            9G                                                       Velvetleaf            9G,9C                                                    Sesbania              8G,8C                                                    Cassia                7G,4C                                                    Mustard               10C                                                      Morningglory          9G,9C                                                    Alfalfa               8G,4C                                                    Jimsonweed            0                                                        Cocklebur             10P,2C                                                   ______________________________________                                    

The data indicate that the compound tested provides excellent post-emergence control of broadleaved weeds in soybeans.

Test H

Test samples of compound 17 were formulated in a non-phytotoxic solvent and applied to the water surface of tub-paddies, three days after transplanting of rice plants into the paddies. The paddy soil contained various weed propagules which were sprouting (except for Scirpus, as explained below). The paddies were maintained in a greenhouse, and plant response ratings (TABLE) were taken about six weeks after application.

                  TABLE H                                                          ______________________________________                                         Rate,        Barnyard- Water    Arrow-                                         g ai/ha                                                                              Rice   grass*    Chestnut*                                                                               head*  Scirpus*                                ______________________________________                                         2.5   0       9E       7G,2C    6G,3H  --                                      10    0      10E       10C      9G,7C  --                                      20    0      10E       9G,9C    10G,2C --                                      ______________________________________                                          *Echinochloa sp., Eleocharis sp., Sagittaria sp., and Scirpus sp. Scirpus      failed to become established and could not be rated.                     

The data above demonstrate excellent control of weeds that are often found in rice cultures and excellent rice tolerance to the application. 

What is claimed is:
 1. A compound of the formula: ##STR92## where W is O or S;Q is O or NR₅ ; R₁ is C₁ -C₄ alkyl, C₁ -C₄ alkyl substituted with 1-3 atoms of F, Cl or Br, CH₂ CH₂ OCH₃, CH₂ CH₂ CH₂ OCH₃ or ##STR93## R₂ is H. F, Cl, Br, OCH₃, NO₂, CF₃ or C₁ -C₂ alkyl; R₃ is H, F, Cl, Br or CH₃ ; R₄ is H, CH₃ or OCH₃ ; R₅ is C₁ -C₄ alkyl; R₆ and R₇ are independently H, F, Cl, Br, CH₃, CF₃, NO₂ or OCH₃ ; A is ##STR94## n is 1 or 2; X₁ is O or CH₂ ; and Y₁ is H, CH₃, OCH₃ or Cl;and provided that: (1) when W is S, then R₄ is H; and (2) when R₄ is OCH₃, when Q is O.
 2. A compound of claim 1 where R₅ is CH₃, W is O, and R₄ is H or CH₃.
 3. A compound of claim 2 where R₁ is C₁ -C₄ alkyl, CF₃, CH₂ CH₂ OCH₃ or CH₂ CH₂ CH₂ OCH₃.
 4. A compound of claim 3 where R₂ is H or Cl.
 5. A compound of claim 4 where R₃ is H.
 6. A compound of claim 5 where R₁ is C₁ -C₃ alkyl or CF₃ and Q is O.
 7. A compound of claim 6 where R₄ is H.
 8. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 1 and at least one of the following: surfactant, solid or liquid diluent.
 9. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 2 and at least one of the following: surfactant, solid or liquid diluent.
 10. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 3 and at least one of the following: surfactant, solid or liquid diluent.
 11. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 4 and at least one of the following: surfactant, solid or liquid diluent.
 12. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 5 and at least one of the following: surfactant, solid or liquid diluent.
 13. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 6 and at least one of the following: surfactant, solid or liquid diluent.
 14. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 7 and at least one of the following: surfactant, solid or liquid diluent.
 15. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 1. 16. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 2. 17. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 3. 18. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 4. 19. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 5. 20. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 6. 21. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 7. 